Cyclopropanemethanamine → HCID 57917646, compound

HRID 1878337Notes

Reaction equation

HRID 1878337 reaction equation
[C:1](=[O:12])(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[NH2:13][C:14]1[C:41]([F:42])=[CH:40][C:17]([C:18]([N:20]2[CH2:25][CH2:24][N:23]([CH2:26][C:27]3[CH:28]=[C:29]([CH:37]=[CH:38][CH:39]=3)[C:30]([NH:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:22][CH2:21]2)=[O:19])=[CH:16][C:15]=1[F:43].[CH:44]1([CH2:47][NH2:48])[CH2:46][CH2:45]1.C(N(C(C)C)C(C)C)C>ClCCl>[C:33]([NH:32][C:30](=[O:31])[C:29]1[CH:37]=[CH:38][CH:39]=[C:27]([CH2:26][N:23]2[CH2:22][CH2:21][N:20]([C:18](=[O:19])[C:17]3[CH:40]=[C:41]([F:42])[C:14]([NH:13][C:1]([NH:48][CH2:47][CH:44]4[CH2:46][CH2:45]4)=[O:12])=[C:15]([F:43])[CH:16]=3)[CH2:25][CH2:24]2)[CH:28]=1)([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 4

HCID 75646CyclopropanemethanamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 57917695HCID 57917695, compound

Product 1

HCID 57917646HCID 57917646, compoundYield 118.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of bis(trichloromethyl) carbonate (0.353 mmol, 105 mg) in dichloromethane (10 mL) was added a solution of 3-((4-(4-amino-3,5-difluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (0.929 mmol. 400 mg) and N-ethyl-N-iosopropylpropan-2-amine (0.3 mL) in dichloromethane (10 mL) (dropwise). After 2 hours stirring, a solution of cyclopropylmethylamine (1.022 mmol, 0.089 mL, 72.7 mg) and N-ethyl-N-isopropylpropan-2-amine (0.222 mL) in dichloromethane (10 mL) was added. The reaction mixture was stirred for 24 hours. Chromatography on silica (eluting with dichloromethane then dichloromethane/methanol (1% to 5%)) gave the title compound (220 mg). MS (ESI) m/z 528.3 [M+H]+

Workup

  1. stirringThe reaction mixture was stirred for 24 hours
  2. washChromatography on silica (eluting with dichloromethane

Sources & evidence

ORD record
ord-b9c6b1701ff8435c8415c4b7425e7e63
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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