Cyclopropylamine → HCID 57849879, compound

HRID 737192Notes

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=NC2[CH:44]=[CH:45][CH:46]=[N:47]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1(N)CC1>>[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:47][CH:46]3[CH2:44][CH2:45]3)=[CH:25][CH:24]=2)=[CH:21][N:22]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 69828Cyclopropylamine

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 57849879HCID 57849879, compound

Procedure

From (S)-2-[5-(4-carboxy-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (Compound 5353, Example 353, 0.04 g, 0.09 mmol), HATU (0.044 g, 0.12 mmol), and (0.03 mL, 0.36 mmol) of cyclopropylamine using General Procedure 3F. 1HNMR (DMSO-d6) δ(ppm)12.44-12.42 (d, 1H), 8.43 (s, 1H), 7.99-7.65 (m, 5H), 7.35-7.10 (m, 4 H), 5.06-4.89 (m, 2H), 4.5-4.46 (m, 1H), 2.83 (s, 2H), 2.25 (m, 1H), 1.91 (m, 3H), 0.70-0.57, (m, 4H); MS: 491.1 (M+H+).

Sources & evidence

ORD record: ord-7d91a35819134fa5bf63cc14af05c3db
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595398B2

Reaction notes

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