Cyclopropanemethanamine → HCID 42628062, compound

HRID 1162624Notes

Reaction equation

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

Participants

Reactant 2

HCID 75646Cyclopropanemethanamine

HCID 58748169HCID 58748169, compound

Product 2

HCID 42628062HCID 42628062, compound

HCID 58748160HCID 58748160, compound

Procedure

Using general procedure D (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-1-{[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-methyl}-pyrrolidine-2-carboxylic acid (example 12) was coupled with aminomethylcyclopropane to give (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]—1-{[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-methyl}-pyrrolidine-2-carboxylic acid cyclopropylmethyl-amide and (2R,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-1-{[2-fluoro-4-(2-oxo-pyridin-1-yl)-phenylcarbamoyl]-methyl}-pyrrolidine-2-carboxylic acid cyclopropylmethyl-amide. White solid (both products). MS 572.3 ([M+H]+)

Sources & evidence

ORD record: ord-a38f6f6286b548079fa610e44b0580e5
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820699B2

Reaction notes

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