Acetic Anhydride → HCID 24937417, compound

HRID 1865296Notes

Reaction equation

[CH3:1][C:2]1[C:7]([C:8]([N:10]2[CH2:17][CH:16]3[CH:12]([CH2:13][N:14]([CH2:18][CH2:19][C:20]4([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH2:24][CH2:23][NH:22][CH2:21]4)[CH2:15]3)[CH2:11]2)=[O:9])=[C:6]([CH3:31])[N:5]=[C:4]([C:32]#[N:33])[CH:3]=1.[F:34][C:35]1([F:42])[CH2:38][CH:37]([C:39](O)=[O:40])[CH2:36]1.C1(C(Cl)=O)CCCC1.C1(CC(Cl)=O)CCCC1.C(OC(=O)C)(=O)C.C(Cl)(=O)C(C)(C)C>>[F:34][C:35]1([F:42])[CH2:38][CH:37]([C:39]([N:22]2[CH2:23][CH2:24][C:20]([CH2:19][CH2:18][N:14]3[CH2:13][CH:12]4[CH2:11][N:10]([C:8]([C:7]5[C:2]([CH3:1])=[CH:3][C:4]([C:32]#[N:33])=[N:5][C:6]=5[CH3:31])=[O:9])[CH2:17][CH:16]4[CH2:15]3)([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:21]2)=[O:40])[CH2:36]1

Participants

Reactant 6

HCID 7918Acetic Anhydride

HCID 62493Pivaloyl chloride

HCID 78284Cyclopentanecarbonyl chloride

HCID 3485182Cyclopentylacetyl chloride

HCID 137777893,3-Difluorocyclobutane-1-carboxylic acid

HCID 68575668HCID 68575668, compound

Product 1

HCID 24937417HCID 24937417, compound

Procedure

The following were prepared analogously from 4,6-dimethyl-5-{5-[2-(3-phenyl-pyrrolidin-3-yl)-ethyl]-hexahydro-pyrrolo[3,4-c]pyrrole-2-carbonyl}-pyridine-2-carbonitrile using the acylating agent in parenthesis in place of 3,3-difluorocyclobutane-carboxylic acid in the final step according to the procedure in step 8 of example 5: III-5 (cyclopentanecarbonyl chloride): III-6 (cyclopentyl-acetyl chloride), III-7 (acetic anhydride) and III-8 (pivaloyl chloride).

Sources & evidence

ORD record: ord-65cd3327f5674786a4707259e4b1ceda
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625905B2

Reaction notes

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