Chlorosuccinimide → HCID 57826439, compound

HRID 1845692Notes

Reaction equation

CC([N:5]([CH2:9][C@@H:10]([NH:18][C:19]([C:21]1[S:22][CH:23]=[C:24]([C:26]2[N:30]([CH3:31])[N:29]=[N:28][CH:27]=2)[CH:25]=1)=[O:20])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)C(=O)[O-])(C)C.C1C(=O)N([Cl:39])C(=O)C1>>[NH2:5][CH2:9][C@@H:10]([NH:18][C:19]([C:21]1[S:22][CH:23]=[C:24]([C:26]2[N:30]([CH3:31])[N:29]=[N:28][C:27]=2[Cl:39])[CH:25]=1)=[O:20])[CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Reactant 2

HCID 31398Chlorosuccinimide

HCID 86633570HCID 86633570, compound

Product 1

HCID 57826439HCID 57826439, compound

Procedure

The title compound was prepared as an off white solid according to the procedure of 261, except substituting 1,1-dimethylethyl[(2S)-2-({[4-(1-methyl-1H-1,2,3-triazol-5-yl)-2-thienyl]carbonyl}amino)-3-cyclohexylpropyl]carbamate (100 mg, 0.22 mmol) for 1,1-dimethylethyl[(2S)-2-({[4-(1-methyl-1H-1,2,3-triazol-5-yl)-2-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate, and the amount of NCS was reduced to leg. LCMS (ES) m/z 382.2 (M+H)+, 1H NMR (400 MHz, METHANOL-d4) δppm 8.15 (d, J=1 Hz, 1H), 8.08 (d, J=1 Hz, 1H), 4.45 (m, 1H), 4.16 (s, 3H), 3.14 (m 1H), 3.05 (m, 1H), 2.00-0.90 (m, 13H).

Sources & evidence

ORD record: ord-585390e67fb64ce7b381e72e3984dd25
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946278B2

Reaction notes

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