N-Hydroxysuccinimide S-acetylthioacetate → HCID 86720322, compound

HRID 928342

Reaction equation

[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:26]3[CH2:30][CH2:29][CH2:28][NH:27]3)=[N:9][C:10]=2[C:11]2[CH:25]=[CH:24][C:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[O:16])=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[C:31]([S:34][CH2:35][C:36](ON1C(=O)CCC1=O)=[O:37])(=[O:33])[CH3:32]>>[C:31](=[O:33])([S:34][CH2:35][C:36]([N:27]1[CH2:28][CH2:29][CH2:30][C@H:26]1[C:8]1[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]2=[C:10]([C:11]2[CH:25]=[CH:24][C:14]([C:15](=[O:16])[NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[CH:13][CH:12]=2)[N:9]=1)=[O:37])[CH3:32]

Participants

Reactant 2

HCID 127532N-Hydroxysuccinimide S-acetylthioacetate

HCID 71226368Acalabrutinib Intermediate

Product 1

HCID 86720322HCID 86720322, compoundYield 31.8%

Procedure

This compound was prepared, in an analogous manner as described in Example 1, from the compound described in intermediate 2b and 2,5-dioxopyrrolidin-1-yl 2-(acetylthio)acetate, to afford the title compound (12.3 mg, 31.8%). Data: UPLC (C) R: 1.51 min; m/z 516.3 (M+H)+.

Workup

customThis compound was prepared, in an analogous manner

Sources & evidence

ORD record: ord-bb823ed57013428c84233add4cbfec05
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290504B2

Linked notes

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