Ammonium Chloride → HCID 178455837, compound

HRID 2364701Notes

Reaction equation

HRID 2364701 reaction equation
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:28](O)=[O:29])=[C:21]5[C:25]=4[O:24][C:23]([CH3:27])([CH3:26])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:31])[C:8](=[O:32])[C@H:7]2[CH2:33][CH3:34])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:35]1([CH2:38][N:39]2[CH2:44][CH2:43][N:42]([C@H:45]3[CH2:50][CH2:49][C@H:48]([NH2:51])[CH2:47][CH2:46]3)[CH2:41][CH2:40]2)[CH2:37][CH2:36]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.[Cl-].[NH4+]>ClCCl>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([NH:16][C:17]4[CH:18]=[CH:19][C:20]([C:28]([NH:51][C@H:48]5[CH2:47][CH2:46][C@H:45]([N:42]6[CH2:41][CH2:40][N:39]([CH2:38][CH:35]7[CH2:36][CH2:37]7)[CH2:44][CH2:43]6)[CH2:50][CH2:49]5)=[O:29])=[C:21]5[C:25]=4[O:24][C:23]([CH3:27])([CH3:26])[CH2:22]5)[N:12]=[CH:11][C:10]=3[N:9]([CH3:31])[C:8](=[O:32])[C@H:7]2[CH2:33][CH3:34])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 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 178511579HCID 178511579, compound

Product 1

HCID 178455837HCID 178455837, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-[[(7R)-8-Cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylic acid 4f (150 mg, 0.32 mmol), (trans)-4-[4-(cyclopropylmethyl)piperazin-1-yl]cyclohexanamine 16b (76 mg, 0.32 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetra methyluronium tetrafluoroborate (103 mg, 0.32 mmol) were dissolved in 20 mL of dichloromethane followed by the addition of diisopropylethylamine (103 mg, 0.80 mmol). The reaction solution was stirred for 2 hours. The resulting solution was added with 20 mL of saturated ammonium chloride solution, seperated, the organic phase was dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was purified by preparation plate to obtain the title compound 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-N-[(trans)-4-[4-(cyclopropylmethyl)piperazin-1-yl]cyclohexyl]-2,2-dimethyl-3H-benzofuran-4-carboxamide 16 (130 mg, yield: 59.0%) as a white solid.

Workup

  1. customseperated
  2. dry with materialthe organic phase was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by preparation plate

Sources & evidence

ORD record
ord-c2d8509f6075435c87d2acd12575a77e
Source dataset
uspto-grants-2014_04
Patent number
US08691822B2

Reaction notes

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