Diisopropylethylamine → HCID 178455839, compound

HRID 2364703Notes

Reaction equation

HRID 2364703 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][CH2:9]2)[CH2:4][CH2:3]1.[CH:15]1([N:20]2[C:29]3[N:28]=[C:27]([NH:30][C:31]4[CH:32]=[CH:33][C:34]([C:42](O)=[O:43])=[C:35]5[C:39]=4[O:38][C:37]([CH3:41])([CH3:40])[CH2:36]5)[N:26]=[CH:25][C:24]=3[N:23]([CH3:45])[C:22](=[O:46])[C@H:21]2[CH2:47][CH3:48])[CH2:19][CH2:18][CH2:17][CH2:16]1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH:15]1([N:20]2[C:29]3[N:28]=[C:27]([NH:30][C:31]4[CH:32]=[CH:33][C:34]([C:42]([NH:14][C@H:11]5[CH2:12][CH2:13][C@H:8]([N:5]6[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]6)[CH2:9][CH2:10]5)=[O:43])=[C:35]5[C:39]=4[O:38][C:37]([CH3:40])([CH3:41])[CH2:36]5)[N:26]=[CH:25][C:24]=3[N:23]([CH3:45])[C:22](=[O:46])[C@H:21]2[CH2:47][CH3:48])[CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 681074737-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylic acidHCID 178481017HCID 178481017, compound

Product 1

HCID 178455839HCID 178455839, compoundYield 36.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude compound (trans)-4-(4-methylpiperazin-1-yl)cyclohexanamine 17b (60 mg, 0.30 mmol), 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylic acid 4f (153 mg, 0.33 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (96 mg, 0.30 mmol) and diisopropylethylamine (96 mg, 0.75 mmol) were dissolved in 25 mL of dichloromethane. The reaction solution was stirred for 2 hours. The resulting solution was added dropwise with saturated sodium bicarbonate solution to adjust pH to 8 to 9, extracted with dichloromethane (30 mL×3), then dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-N-[(trans)-4-(4-methylpiperazin-1-yl)cyclohexyl]-3H-benzofuran-4-carboxamide 17 (70 mg, yield: 33.0%) as a white solid.

Workup

  1. extractionextracted with dichloromethane (30 mL×3)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-980ea84feeb044be8471db4a519c7f1a
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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