Cyclopentylamine → HCID 57849752, compound

HRID 737204Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:32])[NH:17][C:18]1[S:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29](O)=[O:30])=[CH:25][CH:24]=2)=[CH:21][N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:57]1([NH2:62])[CH2:61][CH2:60][CH2:59][CH2:58]1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:32])[NH:17][C:18]1[S:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29](=[O:30])[NH:62][CH:57]3[CH2:61][CH2:60][CH2:59][CH2:58]3)=[CH:25][CH:24]=2)=[CH:21][N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 2906Cyclopentylamine

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

HCID 86616438HCID 86616438, compound2×

Product 1

HCID 57849752HCID 57849752, compound

Procedure

From (S)-2-[5-(4-Carboxy-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (Compound 5353, example 353, 0.03 g, 0.07 mmol), HATU (0.033 g, 0.086 mmol), and (0.03 mL, 0.26 mmol) of cyclopentylamine using General Procedure 3F. 1HNMR (DMSO-d6) δ(ppm)12.42 (m, 0.7H), 8.30-8.27 (d, 1H), 7.80-7.11 (m, 10H), 5.06-4.89 (m, 2 H), 4.50 (m, 1H), 3.51-3.48 (m, 1H), 2.26 (m, 1H), 1.89-1.52 (m, 9H), 1.14 (s, 1H); MS: 519.2 (M+H+).

Sources & evidence

ORD record: ord-caa4cd221c0e49b6bf76cdcc8869ce8f
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595398B2

Reaction notes

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