2-Thiopheneacetyl chloride → HCID 57737259, compound

HRID 1157557Notes

Reaction equation

HRID 1157557 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([O:30][CH2:31][CH2:32][CH2:33][N:34]5[CH2:38][CH2:37][CH2:36][CH2:35]5)[CH:25]=4)[N:18]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[S:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[CH2:44][C:45](Cl)=[O:46]>>[N:34]1([CH2:33][CH2:32][CH2:31][O:30][C:26]2[CH:25]=[C:24]([NH:23][C:19]3[N:18]=[C:17]([C:16]4[C:8]([C:4]5[CH:3]=[C:2]([NH:1][C:45](=[O:46])[CH2:44][C:40]6[S:39][CH:43]=[CH:42][CH:41]=6)[CH:7]=[CH:6][CH:5]=5)=[N:9][N:10]5[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=45)[CH:22]=[CH:21][N:20]=3)[CH:29]=[CH:28][CH:27]=2)[CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

3

Reactant 2

HCID 1623622-Thiopheneacetyl chlorideHCID 57737222HCID 57737222, compound

Product 1

HCID 57737259HCID 57737259, compoundYield 51%

Procedure

The title compound was synthesized from 4-[2-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl]-N-(3-{[3-(1-pyrrolidinyl)propyl]oxy}phenyl)-2-pyrimidinamine using acylation with 2-thienylacetyl chloride as described in Example 10, Step E to yield a light brown solid in 51% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 1.6 (s, 4H) 1.8 (s, 2H) 2.4 (s, 4H) 3.9 (s, 2H) 3.9 (d, J=6.2 Hz, 2H) 6.5 (m, 2H) 7.0 (m, 2H) 7.1 (m, 2H) 7.3 (ddd, J=6.3, 1.3, 1.2 Hz, 2H) 7.4 (m, 3H) 7.5 (t, J=2.3 Hz, 1H) 7.7 (m, 1H) 7.9 (d, J=1.8 Hz, 1H) 8.2 (d, J=5.1 Hz, 1H) 8.5 (s, 1H) 8.8 (m, 1H) 9.5 (s, 1H) 10.3 (s, 1H). ES-LC/MS m/z 630 [M+H]+.

Workup

  1. customto yield a light brown solid in 51% yield

Sources & evidence

ORD record
ord-561db04cf13a4007837e329e75656327
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

Loading…