Hydrochloric Acid → HCID 67051641, compound

HRID 605747Notes

Reaction equation

HRID 605747 reaction equation
CC([N:5]([C@@H:9]([C:11]1([OH:34])[CH2:14][N:13]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[C:18]=2[NH:25][C:26]2[CH:31]=[CH:30][C:29]([I:32])=[CH:28][C:27]=2[F:33])=[O:16])[CH2:12]1)[CH3:10])C(=O)[O-])(C)C.[ClH:35]>CO>[ClH:35].[NH2:5][C@@H:9]([C:11]1([OH:34])[CH2:14][N:13]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[C:18]=2[NH:25][C:26]2[CH:31]=[CH:30][C:29]([I:32])=[CH:28][C:27]=2[F:33])=[O:16])[CH2:12]1)[CH3:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 866458471,1-dimethylethyl{(1R)-1-[1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-hydroxyazetidin-3-yl]ethyl}carbamate

Product 1

HCID 67051641HCID 67051641, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1,1-dimethylethyl{(1R)-1-[1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-hydroxyazetidin-3-yl]ethyl}carbamate (333 mg, 0.56 mmol) in methanol (10 mL) was treated with hydrochloric acid (4 N in dioxane, 1.4 mL, 5.6 mmol) at 60° C. for 30 min. After cooling, the volatile materials were removed in vacuo to provide 3-[(1R)-1-aminoethyl]-1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)azetidin-3-ol hydrochloride as a white solid (285 mg, 0.54 mmol, 97% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.56 (s, 1H), 7.83 (br s, 3H), 7.59 (dd, 1H), 7.39 (d, 1H), 7.34 (m, 1H), 7.21 (q, 1H), 6.69 (m, 1H), 6.65 (s, 1H), 4.25 (dd, 1H), 4.10 (dd, 1H), 3.98 (dd, 1H), 3.80 (m, 1H), 3.48 (m, 1H), 1.11 (dd, 3H); MS (EI) for C18H17F3IN3O2: 492 (MH+)

Workup

  1. temperatureAfter cooling
  2. customthe volatile materials were removed in vacuo

Sources & evidence

ORD record
ord-1ca3e5a680bc44c0bdaad7433420d61a
Source dataset
uspto-grants-2011_03
Patent number
US07915250B2

Reaction notes

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