Isopropanol → HCID 71625160, compound

HRID 589611Notes

Reaction equation

HRID 589611 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]=[C:39]([CH3:42])[CH:40]=3)[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]=[C:39]([CH3:42])[CH:40]=3)[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 71625398HCID 71625398, compoundHCID 71625872HCID 71625872, compound

Product 1

HCID 71625160HCID 71625160, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the method used to prepare 24a, 1b (0.21 mmol) and oxalyl chloride in THF followed by allowing the intermediate acid chloride to react with 2-propanol (2 mL) provided 44 mg (58%) of product 12 as a white solid, mp 172-174° C. 1H NMR (300 MHz, DMSO-d6) δ 1.18-1.24 (m, 6H), 2.35 (s, 3H), 5.09-5.12 (m, 1H), 7.04 (dd, J=2, 9 Hz, 2H), 7.19 (d, J=8, 1H), 7.25-7.30 (m, 3H), 7.46 (dd, J=2, 9 Hz, 1H), 12.34 (s, 1H). LC-MS (CI): m/z 360.0 [(M+H)+ C19H18ClNO2S requires 359.07]. Purity (100%). Calcd for C19H18ClNO2S: C, 63.41; H, 5.04; N, 3.89; S, 8.91; Cl, 9.85. Found: C, 63.59; H, 4.97; N, 3.90; S, 9.04; Cl, 9.85.

Sources & evidence

ORD record
ord-94669dbceecd45f5a066da9254e2fb71
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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