Hydrochloric Acid → HCID 73438520, compound

HRID 521953Notes

Reaction equation

HRID 521953 reaction equation
C(OC([NH:8][C:9]1[S:13][C:12]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=2[F:21])=[N:11][C:10]=1[C:22]([NH:24][C:25]1[CH:29]=[N:28][N:27]([CH3:30])[C:26]=1[CH:31]1[CH2:37][O:36][CH2:35][CH:34]([NH:38]C(=O)OC(C)(C)C)[CH2:33][CH2:32]1)=[O:23])=O)(C)(C)C.Cl>O1CCOCC1.CO>[NH2:8][C:9]1[S:13][C:12]([C:14]2[C:15]([F:21])=[CH:16][CH:17]=[CH:18][C:19]=2[F:20])=[N:11][C:10]=1[C:22]([NH:24][C:25]1[CH:29]=[N:28][N:27]([CH3:30])[C:26]=1[CH:31]1[CH2:32][CH2:33][CH:34]([NH2:38])[CH2:35][O:36][CH2:37]1)=[O:23]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86713884HCID 86713884, compound

Product 1

HCID 73438520HCID 73438520, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl N-[6-[4-[[5-(tert-butoxycarbonylamino)-2-(2,6-difluorophenyl)thiazole-4-carbonyl]amino]-2-methyl-pyrazol-3-yl]oxepan-3-yl]carbamate was stirred with 4N HCl in dioxane (5 mL) and methanol (2 mL) at room temperature for 3 h. The solvent was removed under reduced pressure, basified with saturated NaHCO3, and extracted with ethyl acetate (3×). The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure and the residue purified by preparative HPLC to afford 143 (24 mg, 32%). 1H NMR (400 MHz, DMSO) δ 9.73, 9.56 (s, 1H), 7.83, 7.78 (s, 1H), 7.62-7.42 (m, 3H), 7.36-7.18 (m, 2H), 3.96-3.71 (m, 6H), 3.59 (ddd, J=71.3, 12.2, 4.1 Hz, 1H), 3.03-2.91 (m, 1H), 2.94-2.79 (m, 1H), 2.10-1.89 (m, 1H), 1.85-1.68 (m, 1H), 1.68-1.56 (m, 1H), 1.54-1.39 (m, 1H). LCMS (ES+) m/z 449 (M+1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. customthe solvent removed under reduced pressure
  5. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-4c3f3d1b24cd4de0a09fbbb4e2241d88
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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