2-Bromo-N-cyclopropylacetamide → 2-(4-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}piperazin-1-yl)-N-cyclopropyl-acetamide

HRID 1241405Notes

Reaction equation

[N:1]1([C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[S:15][C:16]([C:19]#[N:20])=[CH:17][N:18]=3)[CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:22][C:23]([NH:25][CH:26]1[CH2:28][CH2:27]1)=[O:24]>C(Cl)(Cl)Cl>[C:19]([C:16]1[S:15][C:14]([NH:13][C:9]2[N:10]=[CH:11][N:12]=[C:7]([N:1]3[CH2:6][CH2:5][N:4]([CH2:22][C:23]([NH:25][CH:26]4[CH2:28][CH2:27]4)=[O:24])[CH2:3][CH2:2]3)[CH:8]=2)=[N:18][CH:17]=1)#[N:20]

Participants

Conditions

Temperature: 100 °C

Procedure

12-3 (0.2 g, 0.39 mmol) and 2-bromo-N-cyclopropylacetamide 38-1 (0.069 g, 0.39 mmol) were suspended in chloroform/2M Na2CO3 in a sealed tube and heated in a Smith Personal Chemistry microwave reactor at 100° C. for 20 minutes. The solid was then filtered off and purified on a silica column to afford 38-2. Hi-Res MS: calc: 385.1554 found: 385.1548. 1H-NMR (CD3OD): 8.39(s, 1H); 7.99(s, 1H); 6.14(s, 1H); 3.68(m, 4H); 3.05(s, 2H); 2.70(m, 1H); 2.58(m, 4H); 0.75(m, 2H); 0.55(m, 2H).

Workup

filtrationThe solid was then filtered off
custompurified on a silica column
customto afford 38-2

Sources & evidence

ORD record: ord-5016891323dc491ca8501aece2c21615
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115597B2

Reaction notes

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