4-Nitrobenzyl chloroformate → HCID 136346637, compound

HRID 220809Notes

Reaction equation

HRID 220809 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=[O:3].Cl.[CH3:16][N:17]1[C:26]2[NH:25][C:24]3[CH:27]=[C:28]([CH3:31])[CH:29]=[CH:30][C:23]=3[N:22]([C:32]([CH:34]3[CH2:39][CH2:38][CH:37]([CH2:40][NH:41][C:42](=[O:50])[CH2:43][CH:44]4[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]4)[CH2:36][CH2:35]3)=[O:33])[CH2:21][C:20]=2[CH:19]=[N:18]1>ClCCl.C(N(CC)CC)C>[N+:12]([C:9]1[CH:10]=[CH:11][C:6]([CH2:5][O:4][C:2]([N:47]2[CH2:48][CH2:49][CH:44]([CH2:43][C:42](=[O:50])[NH:41][CH2:40][CH:37]3[CH2:36][CH2:35][CH:34]([C:32]([N:22]4[CH2:21][C:20]5[CH:19]=[N:18][N:17]([CH3:16])[C:26]=5[NH:25][C:24]5[CH:27]=[C:28]([CH3:31])[CH:29]=[CH:30][C:23]4=5)=[O:33])[CH2:39][CH2:38]3)[CH2:45][CH2:46]2)=[O:3])=[CH:7][CH:8]=1)([O-:14])=[O:13]

Participants

5

Reactant 2

HCID 782054-Nitrobenzyl chloroformateHCID 136346634HCID 136346634, compound

Product 1

HCID 136346637HCID 136346637, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of 4-nitrobenzyl chloroformate (1.08 mg, 0.005 mmol) in dichloromethane (0.05 ml) was added to a solution of N-[4-(3,6-Dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-cyclohexylmethyl]-2-piperidin-4-yl-acetamide hydrochloride from Example E17 (2.58 mg, 0.005 mmol) in dichloromethane (0.05 ml) and triethylamine (0.0035 ml). The mixture was stirred at room temperature for 1 h then solvents were removed in vacuo to yield the title compound. (ESI)+: [M+H]+=658.5

Workup

  1. customsolvents were removed in vacuo

Sources & evidence

ORD record
ord-e1b274b08f7e42ea9aef8a22e96318ce
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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