Methanol → HCID 75217891, compound

HRID 1951600Notes

Reaction equation

[S:1]([OH:5])(=[O:4])(=[O:3])[CH3:2].[F:6][C@@H:7]1[CH2:11][N:10]([C:12](=[O:26])[CH2:13][NH:14][C@@H:15]2[CH2:19][CH2:18][C@H:17]([CH2:20][N:21]3[CH:25]=[N:24][CH:23]=[N:22]3)[CH2:16]2)[C@H:9]([C:27]#[N:28])[CH2:8]1.CO>C(OCC)(=O)C>[S:1]([OH:5])(=[O:4])(=[O:3])[CH3:2].[F:6][CH:7]1[CH2:11][N:10]2[C:12](=[O:26])[CH2:13][N:14]([CH:15]3[CH2:19][CH2:18][CH:17]([CH2:20][N:21]4[CH:25]=[N:24][CH:23]=[N:22]4)[CH2:16]3)[C:27](=[NH:28])[CH:9]2[CH2:8]1

Participants

Conditions

Temperature: 27.5 °C

Procedure

(2S,4S)-4-fluoro-1-({[(1R,3S)-3-(1H-1,2,4-triazol-1-ylmethyl)-cyclopentyl]amino}acetyl)pyrrolidine-2-carbonitrile mesylate salt was melted at 150-160° C. for 3 to 4 h and the residue was cooled to 25-30° C. To this, a mixture of methanol (100 ml, 2 vol.) and ethyl acetate (250 ml, 5 vol.) was added and heated at 50-55° C. The reaction mixture on cooling to 25-30° C. precipitates 7-fluoro-1-imino-2-[(3S,1R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentyl]-perhydroazolo[1,2-a]pyrazin-4-one mesylate. 1H NMR (300 MHz, DMSO-d6) δ 1.52-1.88 (m, 6H), 2.21-2.40 (m, 5H), 2.77-2.80 (m, 1H), 3.52-3.83 (m, 2H), 3.95-4.00 (d, 1H), 4.18-4.25 (m, 3H), 4.42 (m, 1H), 4.85 (m, 1H), 5.39-5.56 (d, 1H), 7.98 (s, 1H), 8.54 (s, 1H), 9.17 (s, 2H); ESI-MS (m/z) 321 (100%); 13C NMR (300 MHz, DMSO-d6) δ 27.00, 26.71, 32.04, 35.81, 32.54, 37.74, 39.97, 47.06, 51.85, 51.54, 52.80, 56.02, 57.73, 92.12, 89.82, 144.14, 151.43, 161.74, 162.12.

Workup

customfor 3 to 4 h
additionwas added
temperatureheated at 50-55° C
temperatureThe reaction mixture on cooling to 25-30° C.
customprecipitates 7-fluoro-1-imino-2-[(3S,1R)-3-(1H-1,2,4-triazol-1-ylmethyl)cyclopentyl]-perhydroazolo[1,2-a]pyrazin-4-one mesylate

Sources & evidence

ORD record: ord-055d291dd7a8458d9cd82a96d8f7b3d1
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404727B2

Reaction notes

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