Tetrahydrofuran → HCID 57393705, compound

HRID 1687637Notes

Reaction equation

HRID 1687637 reaction equation
[Cl:1][C:2]1[C:3]([NH:30][C:31]2[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:32]=2[C:33]([NH:35][CH3:36])=[O:34])=[N:4][C:5]([NH:8][C:9]2[CH:29]=[CH:28][C:12]3[C:13]([CH3:27])([CH3:26])[CH2:14][CH:15]([NH:19]C(=O)C(F)(F)F)[C:16](=[O:18])[NH:17][C:11]=3[CH:10]=2)=[N:6][CH:7]=1.[NH4+].[OH-].C1COCC1.[OH-].[Na+]>CO>[NH2:19][CH:15]1[CH2:14][C:13]([CH3:26])([CH3:27])[C:12]2[CH:28]=[CH:29][C:9]([NH:8][C:5]3[N:4]=[C:3]([NH:30][C:31]4[C:40]([F:41])=[CH:39][CH:38]=[CH:37][C:32]=4[C:33]([NH:35][CH3:36])=[O:34])[C:2]([Cl:1])=[CH:7][N:6]=3)=[CH:10][C:11]=2[NH:17][C:16]1=[O:18]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 565977732-{5-Chloro-2-[5,5-dimethyl-2-oxo-3-(2,2,2-trifluoro-acetylamino)-2,3,4,5-tetrahydro-1H-1-benzazepin-8-ylamino]-pyrimidin-4-ylamino}-3-fluoro-N-methyl-benzamide

Product 1

HCID 57393705HCID 57393705, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combined 2-{5-Chloro-2-[5,5-dimethyl-2-oxo-3-(2,2,2-trifluoro-acetylamino)-2,3,4,5-tetrahydro-1H-1-benzazepin-8-ylamino]-pyrimidin-4-ylamino}-3-fluoro-N-methyl-benzamide (355 mg, 0.000598 mol), 1 M of NH4OH in Methanol (2 mL), and THF (50 mL, 0.6 mol). Added 2 mL of 50% NaOH and stirred for 2 hr. Product isolated as a white solid (244 mg, 82%). LCMS 498.22 (M+H), HPLC purity 94%, 1H-NMR (CDCl3, 400 MHz) δ 8.90 (bs, 1H), 8.05 (s, 1H), 7.93 (bs, 1H), 7.63 (bs, 1H), 7.44-7.39 (m, 2H), 7.35-7.31 (m, 2H), 7.28-7.26 (m, 2H), 7.20 (d, J=7.5 Hz, 1H), 6.90 (d, J=8.2 Hz, 1H), 6.71 (bs, 1H), 3.40-3.37 (m, 1H), 2.93 (d, J=4.7 Hz, 3H), 2.31-2.27 (m, 1H), 1.99-1.96 (m, 2H), 1.88-1.85 (m, 1H), 1.38 (s, 3H), 1.28 (s, 3H).

Sources & evidence

ORD record
ord-1d9d8201aab54114affcf031e8fa6172
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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