Cyclopentylacetyl chloride → 2-Cyclopentyl-1-{4-[4-(6-fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidin-1-yl}-ethanone

HRID 731907Notes

Reaction equation

HRID 731907 reaction equation
Cl.[F:2][C:3]1[N:27]=[CH:26][C:6]2[N:7]=[CH:8][N:9]=[C:10]([NH:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)=[C:14]([CH3:25])[CH:13]=3)[C:5]=2[CH:4]=1.[CH:28]1([CH2:33][C:34](Cl)=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29]1.C1(C(N2CCC(OC3C=CC(NC4C5C=C(F)N=CC=5N=CN=4)=CC=3C)CC2)=O)CCCC1>>[CH:28]1([CH2:33][C:34]([N:22]2[CH2:23][CH2:24][CH:19]([O:18][C:15]3[CH:16]=[CH:17][C:12]([NH:11][C:10]4[C:5]5[CH:4]=[C:3]([F:2])[N:27]=[CH:26][C:6]=5[N:7]=[CH:8][N:9]=4)=[CH:13][C:14]=3[CH3:25])[CH2:20][CH2:21]2)=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

4

Reactant 3

HCID 3485182Cyclopentylacetyl chlorideHCID 69051928Cyclopentyl-{4-[4-(6-fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidin-1-yl}-methanoneHCID 69056076(6-Fluoro-pyrido[3,4-d]pyrimidin-4-yl)-[3-methyl-4-(piperidin-4-yloxy)-phenyl]-amine hydrochloride

Product 1

HCID 690526092-Cyclopentyl-1-{4-[4-(6-fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidin-1-yl}-ethanone

Procedure

The title compound was prepared from (6-Fluoro-pyrido[3,4-d]pyrimidin-4-yl)-[3-methyl-4-(piperidin-4-yloxy)-phenyl]-amine (T) and cyclopentylacetyl chloride by a procedure analogous to that described for the synthesis of Cyclopentyl-{4-[4-(6-fluoro-pyrido[3,4-d]pyrimidin-4-ylamino)-2-methyl-phenoxy]-piperidin-1-yl}-methanone. MS: 464.3 (MH+); 1H NMR (DMSO-d6, 400 MHz): δ 9.90 (s, 1H), δ 8.86 (s, 1H), δ 8.57 (s, 1H), δ 8.19 (s, 1H), δ 7.035 (d, J=9.97, 2H), δ 4.58-4.59 (m, 1H), δ 3.71 (m, 2H), δ 3.30-3.93 (m, 2H), δ 2.31 (d, J=7.47, 2H), δ 2.17 (s, 3H), δ 2.08-2.12 (m, 1H), δ 1.80-1.95 (m, 1H), δ 1.43-1.73 (m, 10H), δ 1.05-1.10 (m, 2H).

Sources & evidence

ORD record
ord-429e58aa1ab842e7a76634803e497572
Source dataset
uspto-grants-2009_09
Patent number
US07585869B2

Reaction notes

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