Neopentylamine → HCID 25191885, compound

HRID 1878426Notes

Reaction equation

HRID 1878426 reaction equation
[C:1](=[O:12])(OC(Cl)(Cl)Cl)OC(Cl)(Cl)Cl.[NH2:13][C:14]1[CH:41]=[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][CH:33]3[CH2:36][CH2:35][CH2:34]3)=[O:31])[CH2:22][CH2:21]2)=[O:19])=[CH:16][C:15]=1[F:42].C(N(C(C)C)C(C)C)C.[CH3:52][C:53]([CH3:57])([CH3:56])[CH2:54][NH2:55]>ClCCl>[CH:33]1([NH:32][C:30](=[O:31])[C:29]2[CH:37]=[CH:38][CH:39]=[C:27]([CH2:26][N:23]3[CH2:24][CH2:25][N:20]([C:18](=[O:19])[C:17]4[CH:40]=[CH:41][C:14]([NH:13][C:1]([NH:55][CH2:54][C:53]([CH3:57])([CH3:56])[CH3:52])=[O:12])=[C:15]([F:42])[CH:16]=4)[CH2:21][CH2:22]3)[CH:28]=2)[CH2:34][CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 79882NeopentylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 57917659HCID 57917659, compound

Product 1

HCID 25191885HCID 25191885, compoundYield 153.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of bis(trichloromethyl) carbonate (0.331 mmol, 98 mg) in dichloromethane (10 mL) was added a solution of 3-((4-(4-amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-cyclobutylbenzamide (0.974 mmol, 400 mg) and N-ethyl-N-isopropylpropan-2-amine (2.144 mmol, 0.354 mL, 277 mg) in dichloromethane (10 mL) (dropwise). The reaction mixture was stirred for 1 hour then 2,2-dimethylpropan-1-amine (1.169 mmol, 0.137 mL, 102 mg) was added. The reaction mixture was stirred for 20 hours. Chromatography on silica (eluting with dichloromethane to dichloromethane/methanol (1% to 3%)) gave the title compound (266 mg).

Workup

  1. stirringThe reaction mixture was stirred for 20 hours

Sources & evidence

ORD record
ord-0f91326a0fe14b37b70414ab2d2bcfab
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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