Hydrochloric Acid → HCID 178489599, compound

HRID 343240Notes

Reaction equation

HRID 343240 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH:18]2[C:24](=[O:25])[N:23]([CH2:26][C:27]([N:29]([CH:38]([CH3:40])[CH3:39])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])=[O:28])[C:22]3[CH:41]=[CH:42][CH:43]=[CH:44][C:21]=3[N:20]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[C:19]2=[O:51])=[N:9]1)=O)(C)(C)C.Cl.C(OCC)C>O1CCOCC1>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][CH:18]2[C:24](=[O:25])[N:23]([CH2:26][C:27]([N:29]([CH:38]([CH3:40])[CH3:39])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH3:37])=[O:28])[C:22]3[CH:41]=[CH:42][CH:43]=[CH:44][C:21]=3[N:20]([C:45]3[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=3)[C:19]2=[O:51])=[N:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 10532638HCID 10532638, compound

Product 1

HCID 178489599HCID 178489599, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-[3-(1-tert-butoxycarbonyl-1H-indazol-3-ylmethyl)-2,4-dioxo-5-phenyl-2,3,4,5-tetrahydrobenzo[b][1,4]diazepin-1-yl]-N-isopropyl-N-(2-methoxy-phenyl) acetamide, prepared as in Intermediate 73, (260 mg, 0.377 mmol) and 4N HCl in dioxane (2 mL) is stirred at RT for 2 h. Diethyl ether (40 mL) is added and the resultant mixture stirred vigorously for 20 min. The solids were allowed to settle and the solvent is decanted. This procedure is repeated three times and the final gum dried by concentration in vacuo. Recrystallisation from 5% methanol in ethyl acetate afforded the title compound (126 mg) as a white powdery solid, which exists as 3:2 mixture of rotamers (major rotamer recorded): 1H NMR (300 MHz, CDCl3) δ7.98 (t, 1H, J=8.0), 7.70 (m, 1H), 7.61 (s, 1H), 7.40-6.90 (m, 15H), 5.05 (m, 1H, J=6.9), 4.45 (d, 2H, J=16.4), 4.25 (d, 1H, J=17.5), 4.07 (d, 1H, J=16.4), 3.74 (m, 5H), 1.16 (m, 6H); Low resolution MS (FAB) m/e 588 (M+); Tr =27.29 min (RP-HPLC, 100% A to 100% C, 30 min).

Workup

  1. customthe solvent is decanted
  2. customthe final gum dried by concentration in vacuo
  3. customRecrystallisation from 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-9e739729b895401a82b6a46710f2dde8
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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