Hydrochloric Acid → HCID 68565010, compound

HRID 1990926Notes

Reaction equation

HRID 1990926 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3[N:15]=[C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:17]=[C:18](Cl)[C:13]=3[CH:12]=[C:11]2[C:26]([O-:28])=[O:27])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH:30][CH:31](O)[CH2:32][CH2:33][NH2:34].Cl.CS(C)=[O:39]>O>[C:1]1([S:7]([N:10]2[C:14]3[N:15]=[C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:17]=[C:18]([NH:34][CH2:33][C@H:32]([OH:39])[CH2:31][OH:30])[C:13]=3[CH:12]=[C:11]2[C:26]([OH:28])=[O:27])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 5242570HCID 5242570, compoundHCID 59128314HCID 59128314, compound

Product 1

HCID 68565010HCID 68565010, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

27 (126 mg) and dihydroxypropyl amine (273 mg) were stirred in anhydrous DMSO (2 mL) at 80° C. under nitrogen for 4 h. The reaction mixture was cooled to rt and diluted with water (10 mL). The resulting mixture was acidified with 0.5N HCl until a white solid formed (pH≈3.5-4.0). The solid was collected by filtration, washed with cold water, and dried in vacuo. A white solid (131 mg) was obtained in 93% yield. 1H-NMR (200 MHz, DMSO-d6): δ=3.30-3.33 (m, 2H), 3.57-3.60 (m, 2H), 3.65-6.71 (m, 1H), 3.82-3.97 (m, 2H), 7.32 (s, 1H), 7.46-7.50 (m, 3H), 7.55-7.68 (m, 3H), 8.38-8.49 (m, 4H). MS (ES): 468.9 (M++1).

Workup

  1. customformed (pH≈3.5-4.0)
  2. filtrationThe solid was collected by filtration
  3. washwashed with cold water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-aa383b2dc1a74fb19341208332fcdf68
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

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