Neopentylamine → HCID 25191886, compound

HRID 1878431Notes

Reaction equation

HRID 1878431 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][C@@H:33]([CH2:35][CH3:36])[CH3:34])=[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>[C@H:33]([NH:32][C:30](=[O:31])[C:29]1[CH:37]=[CH:38][CH:39]=[C:27]([CH2:26][N:23]2[CH2:24][CH2:25][N:20]([C:18](=[O:19])[C:17]3[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]=3)[CH2:21][CH2:22]2)[CH:28]=1)([CH2:35][CH3:36])[CH3:34]

Participants

6

Reactant 4

HCID 79882NeopentylamineHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 66879318HCID 66879318, compound

Product 1

HCID 25191886HCID 25191886, compoundYield 4.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of bis(trichloromethyl) carbonate (0.989 mmol, 0.294 g) in dichloromethane (30 mL) was added (R)-3-((4-(4-amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-sec-butylbenzamide (2.91 mmol, 1.2 g) and N-ethyl-N-isopropylpropan-2-amine (6.40 mmol, 1.058 mL, 0.827 g) in dichloromethane (30 mL). The reaction mixture was stirred for 1 hour then 2,2-dimethylpropan-1-amine (3.49 mmol, 0.408 ml, 0.304 g) was added. After 2 hours stirring, the crude material was purified by acidic reverse phase LC/MS then by silica chromatography to give the title compound (25 mg).

Workup

  1. stirringAfter 2 hours stirring
  2. customthe crude material was purified by acidic reverse phase LC/MS

Sources & evidence

ORD record
ord-cb634e2f08924bfd9cb3c6d1b6470d5f
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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