HCID 71092888, compound → HCID 89266653, compound

HRID 1522300Notes

Reaction equation

HRID 1522300 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:26])/[CH:17]=[CH:18]/[CH2:19][N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[CH:12]=[CH:13][CH:14]=2)[C:3]=1[C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:29][CH:28]=1.[O:40]=[C:41]1[NH:45][CH:44]2[CH2:46][S:47][C@@H:48]([CH2:49][CH2:50][CH2:51][CH2:52][C:53](OC3C(F)=C(F)C(F)=C(F)C=3F)=[O:54])[CH:43]2[NH:42]1>>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:26])/[CH:17]=[CH:18]/[CH2:19][N:20]3[CH2:25][CH2:24][N:23]([C:53](=[O:54])[CH2:52][CH2:51][CH2:50][CH2:49][C@H:48]4[CH:43]5[CH:44]([NH:45][C:41](=[O:40])[NH:42]5)[CH2:46][S:47]4)[CH2:22][CH2:21]3)[CH:12]=[CH:13][CH:14]=2)[C:3]=1[C:27]1[CH:28]=[CH:29][C:30]([O:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 71092888HCID 71092888, compoundHCID 89266729HCID 89266729, compound

Product 1

HCID 89266653HCID 89266653, compoundYield 45%

Procedure

((E)-N-(3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)phenyl)-4-(4-(5-((4S)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoyl)piperazin-1-yl)but-2-enamide was prepared from (E)-N-(3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)phenyl)-4-(piperazin-1-yl)but-2-enamide and perfluorophenyl 5-((4S)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoate using Method F (45% yield). HPLC: 100%, RT=3.635 min. MS: m/z=750 [M+H]+, RT=1.84 min.

Sources & evidence

ORD record
ord-01990491e26e413a82e274fd4eeee46b
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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