1,2-Dichloroethane → HCID 23657984, compound

HRID 2378993Notes

Reaction equation

HRID 2378993 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[C:8]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:7](=[O:17])[NH:6][C:5]=2[CH:4]=[CH:3]1.[Cl:18][C:19]1[C:27]2[NH:26]N=[CH:24][C:23]=2[C:22]2[CH2:28][N:29]([CH2:38][C:39]([CH3:42])([CH3:41])[CH3:40])[C:30](=[O:37])[C@H:31]([CH2:33][C:34]([OH:36])=O)[CH2:32][C:21]=2[CH:20]=1.[CH:43]1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]2[CH2:32][C@@H:31]([CH2:33][C:34]([N:14]3[CH2:15][CH2:16][CH:11]([C:8]4[C:7](=[O:17])[NH:6][C:5]5[CH:4]=[CH:3][N:2]([CH3:1])[C:10]=5[CH:9]=4)[CH2:12][CH2:13]3)=[O:36])[C:30](=[O:37])[N:29]([CH2:38][C:39]([CH3:42])([CH3:40])[CH3:41])[CH2:28][C:22]2=[C:23]2[C:27]=1[NH:26][CH:43]=[CH:24]2

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59006343HCID 59006343, compoundHCID 59732059HCID 59732059, compound

Product 1

HCID 23657984HCID 23657984, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-methyl-6-(piperidin-4-yl)-1H-pyrrolo[3,2-b]pyridin-5(4H)-one (41 mg, 0.177 mmol), (S)-2-(4-chloro-9-neopentyl-8-oxo-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)acetic acid (64.5 mg, 0.177 mmol), HOBT (26.3 mg, 0.195 mmol) and EDC (37.4 mg, 0.195 mmol) in DMF (2 mL) was added diisopropylethylamine (108 μl, 0.620 mmol) at rt. The resulting mixture was stirred at rt over night, most of the solvent was removed under N2, the residue was purified on reverse phase PrepHPLC to afford a grey gum which was triturated with Et2O (2 mL), filtered and washed with Et2O (2×0.5 mL) to afford the expected product, (S)-7-chloro-4-(2-(4-(1-methyl-5-oxo-4,5-dihydro-1H-pyrrolo [3,2-b]pyridin-6-yl)piperidin-1-yl)-2-oxoethyl)-2-neopentyl-1,2,4,5-tetrahydroazepino[3,4-e]indol-3(8H)-one (32 mg grey solid. Mass spec: 577.30 (MH+) calc. for C31H37ClN6O3 576.26.

Workup

  1. customwas removed under N2
  2. customthe residue was purified on reverse phase PrepHPLC
  3. customto afford a grey gum which
  4. customwas triturated with Et2O (2 mL)
  5. filtrationfiltered
  6. washwashed with Et2O (2×0.5 mL)

Sources & evidence

ORD record
ord-990c8adcb9344c39bfdcbc1cb30ea1b9
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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