Hydrochloric Acid → HCID 68014577, compound

HRID 220179Notes

Reaction equation

HRID 220179 reaction equation
Cl.C(OC(=O)[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:46])/[CH:17]=[CH:18]/[C:19]1[CH:20]=[N:21][C:22]([CH:25]([C:36](=[O:45])[NH:37][C:38]2[CH:43]=[CH:42][C:41]([Br:44])=[CH:40][CH:39]=2)[CH2:26][CH2:27][CH2:28][N:29]2[CH2:34][C@@H:33]3[CH2:35][C@H:30]2[CH2:31][O:32]3)=[CH:23][CH:24]=1)(C)(C)C.C([O-])(O)=O.[Na+]>CO>[Br:44][C:41]1[CH:42]=[CH:43][C:38]([NH:37][C:36](=[O:45])[CH:25]([C:22]2[CH:23]=[CH:24][C:19](/[CH:18]=[CH:17]/[C:16](=[O:46])[NH:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[NH2:8])=[CH:20][N:21]=2)[CH2:26][CH2:27][CH2:28][N:29]2[CH2:34][C@@H:33]3[CH2:35][C@H:30]2[CH2:31][O:32]3)=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68559961HCID 68559961, compound

Product 1

HCID 68014577HCID 68014577, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrochloric acid in methanol (1.25 M, 5 mL) was added to the (E)-[2-(3-{6-[1-(4-Bromo-phenylcarbamoyl)-4-({1S,4S}-2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)-butyl]-pyridin-3-yl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester residue, the mixture was stirred at room temperature for about 12 h, and then NaHCO3 was added to the reaction system. After filtration of solids, the crude mixture was purified by preparative HPLC to obtain white solid. MS: calc'd 590 (MH+), exp 590 (MH+). 1H NMR (d4-MeOD, 400 MHz), 8.76 (d, 1H, J=1.6 Hz), 8.09 (dd, 1H, J=2.0, 8.0 Hz), 7.70 (d, 1H, J=15.6 Hz), 7.61 (d, 1H, J=8.0 Hz), 7.57-7.52 (m, 2H), 7.48-7.43 (m, 2H), 7.21 (d, 1H, J=1.6 Hz), 7.10-7.04 (m, 1H), 6.97 (d, 1H, J=15.6 Hz), 6.90 (d, 1H, J=8.0 Hz), 6.77 (t, 1H, J=8.0 Hz), 4.46 (s, 1H), 4.02 (d, 1H, J=8.4 Hz), 3.95 (t, 1H, J=7.6 Hz), 3.76 (broad s, 1H), 3.66 (d, 1H, J=7.3 Hz), 2.95 (d, 1H, J=10.6 Hz), 2.87 (broad s, 1H), 2.77 (broad s, 2H), 2.24 (broad s, 1H), 2.03 (broad s, 1H), 1.95 (d, 1H, J=10.8 Hz), 1.85 (d, 1H, J=10.8 Hz), 1.63 (broad s, 2H).

Workup

  1. filtrationAfter filtration of solids
  2. customthe crude mixture was purified by preparative HPLC
  3. customto obtain white solid

Sources & evidence

ORD record
ord-6a10a9f34659451d83c4b8b1431c2f24
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

Loading…