Hydrochloric Acid → 5-Bromo-pyridine-2-carboxylic acid [3-((3R*,6R*)-5-amino-3,6-dimethyl-6-tri-fluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-phenyl]-amide hydrochloride

HRID 81569Notes

Reaction equation

HRID 81569 reaction equation
C(OC(=O)[NH:7][C:8]1[C@:9]([CH3:35])([C:31]([F:34])([F:33])[F:32])[O:10][CH2:11][C@:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][N:25]=3)=[O:23])[CH:16]=2)([CH3:14])[N:13]=1)(C)(C)C.[ClH:37]>C1COCC1>[ClH:37].[NH2:7][C:8]1[C@:9]([CH3:35])([C:31]([F:34])([F:32])[F:33])[O:10][CH2:11][C@:12]([C:15]2[CH:16]=[C:17]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][N:25]=3)=[O:23])[CH:18]=[CH:19][CH:20]=2)([CH3:14])[N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86650262HCID 86650262, compound

Product 1

HCID 666659305-Bromo-pyridine-2-carboxylic acid [3-((3R*,6R*)-5-amino-3,6-dimethyl-6-tri-fluoromethyl-3,6-dihydro-2H-[1,4]oxazin-3-yl)-phenyl]-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

((2R*,5R*)-5-{3-[(5-bromo-pyridine-2-carbonyl)-amino]-phenyl}-2,5-dimethyl-2-trifluoromethyl-5,6-dihydro-2H-[1,4]oxazin-3-yl)-carbamic acid tert-butyl ester (0.113 g, 0.194 mmol) was dissolved in THF (1 ml) and 4N HCl (5 ml) and the reaction mixture was stirred for 2 h at 25° C. and 3 h at 40° C. The solvents were removed under reduced pressure and the resulting residue was titurated with Et2O to provide the title compound as a white amorphous solid: TLC (EtOAc/MeOH 9:1): Rf=0.56; HPLC RtH5=1.147 min; 1H NMR (600 MHz, DMSO-d6): δ 11.45 (s, 1H), 10.81 (s, 1H), 9.74 (d, 2H), 8.88 (dd, 1H), 8.34 (dd, 1H), 8.10 (d, 1H), 8.01 (d, 1H), 7.95 (s, 1H), 7.46 (t, 1H), 7.27 (d, 1H), 4.13 (d, 1H), 4.05 (d, 1H), 1.81 (s, 3H), 1.69 (s, 3H); ESIMS: 471, 473 [(M+H)+].

Workup

  1. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-f1c4037938884a02848af11692741bf4
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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