Isopropanol → HCID 71625282, compound

HRID 589615Notes

Reaction equation

HRID 589615 reaction equation
Cl[C:2]1[CH:3]=C(SC2C3C(=CC(C)=CC=3)NC=2CCC(N)=O)C=C(Cl)[CH:7]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][C:33]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][C:40]=3[CH3:42])[NH:35][C:34]=2[C:43]([OH:45])=[O:44])=[CH:28][CH:27]=1.C(Cl)(=O)C(Cl)=O.CC(O)C>C1COCC1>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([S:32][C:33]2[C:41]3[C:36](=[CH:37][CH:38]=[CH:39][C:40]=3[CH3:42])[NH:35][C:34]=2[C:43]([O:45][CH:2]([CH3:3])[CH3:7])=[O:44])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 65578Oxalyl chlorideHCID 71625288HCID 71625288, compoundHCID 71625872HCID 71625872, compound

Product 1

HCID 71625282HCID 71625282, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the method used to prepare 24a, the use of 1a (0.21 mmol) and oxalyl chloride in THF followed by allowing the intermediate acid chloride to react with 2-propanol (2 mL) provided 40 mg (53%) of product 13 as a white solid, mp 190-192° C. 1H NMR (300 MHz, DMSO-d6) δ 1.22 (d, J=6 Hz, 6H), 2.60 (s, 3H), 5.05-5.14 (m, 1H), 6.88 (d, J=8 Hz, 1H), 6.98 (d, J=9 Hz, 2H), 7.23 (t, J=8 Hz, 1H), 7.30 (d, J=9 Hz, 2H), 7.42 (d, J=9 Hz, 1H), 12.45 (s, 1H). LC-MS (CI): m/z 360.1 [(M+H)+ C19H18ClNO2S requires 359.07]. Purity (100%). Calcd for C19H18ClNO2S.0.07CH2Cl2: C, 62.61; H, 5.00; N, 3.83; S, 8.77; Cl, 11.05. Found: C, 62.32; H, 5.01; N, 3.77; S, 9.08; Cl, 10.93.

Sources & evidence

ORD record
ord-97c682b90e3c49509310543da7e7c009
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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