Hydrochloric Acid → HCID 73602993, compound

HRID 1915954Notes

Reaction equation

HRID 1915954 reaction equation
C(OC([NH:8][C:9]1([CH3:48])[CH2:15][CH2:14][N:13]([C:16]2[N:20]([CH3:21])[N:19]=[CH:18][C:17]=2[NH:22][C:23]([C:25]2[N:26]=[C:27]([C:38]3[C:43]([F:44])=[CH:42][CH:41]=[CH:40][C:39]=3[F:45])[S:28][C:29]=2[NH:30]C(=O)OC(C)(C)C)=[O:24])[CH2:12][C:11]([F:47])([F:46])[CH2:10]1)=O)(C)(C)C.Cl.O1CCOCC1>CO>[NH2:30][C:29]1[S:28][C:27]([C:38]2[C:39]([F:45])=[CH:40][CH:41]=[CH:42][C:43]=2[F:44])=[N:26][C:25]=1[C:23]([NH:22][C:17]1[CH:18]=[N:19][N:20]([CH3:21])[C:16]=1[N:13]1[CH2:14][CH2:15][C:9]([NH2:8])([CH3:48])[CH2:10][C:11]([F:46])([F:47])[CH2:12]1)=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86680152HCID 86680152, compound

Product 1

HCID 73602993HCID 73602993, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl N-(4-((5-(5-(tert-butoxycarbonylamino)-3,3-difluoro-5-methyl-azepan-1-yl)-1-methyl-pyrazol-4-yl)carbamoyl)-2-(2,6-difluorophenyl)thiazol-5-yl)carbamate (0.36 g, 0.51 mmol) in MeOH (5 mL) was added HCl in dioxane (4 M, 0.02 mol, 5 mL). The reaction mixture was stirred at room temperature for 16 hr and concentrated under reduced pressure. Purification via SCX cartridge washing with 1/1 MeOH/DCM (250 mL) followed by MeOH (250 mL) and eluting with 1 N NH3 in MeOH (200 mL) gave 495 as a pale yellow foam (250 mg, 87%). 1H NMR (400 MHz, CDCl3) δ 8.92 (s, 1H), 7.85 (s, 1H), 7.33 (tt, J=8.4, 6.1 Hz, 1H), 7.07-6.99 (m, 2H), 6.28-6.06 (m, 2H), 3.78-3.74 (m, 3H), 3.65-3.40 (m, 3H), 3.29-3.20 (m, 1H), 2.41-2.16 (m, 2H), 1.96-1.85 (m, 1H), 1.77 (dt, J=14.7, 4.6 Hz, 1H), 1.26 (s, 3H). Exchangeables not observed. LCMS (ES+) m/z 498 (M+1)

Workup

  1. concentrationconcentrated under reduced pressure
  2. customPurification via SCX cartridge
  3. washwashing with 1/1 MeOH/DCM (250 mL)
  4. washeluting with 1 N NH3 in MeOH (200 mL)

Sources & evidence

ORD record
ord-38a5d2626ee0442b87ba895dfc3029f8
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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