Hydrochloric Acid → HCID 68556702, compound

HRID 220175Notes

Reaction equation

HRID 220175 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:45])/[CH:17]=[CH:18]/[C:19]1[CH:24]=[CH:23][C:22]([CH:25]([C:35](=[O:44])[NH:36][C:37]2[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=2)[CH2:26][CH2:27][N:28]2[CH2:33][C@@H:32]3[CH2:34][C@H:29]2[CH2:30][O:31]3)=[CH:21][CH:20]=1)(C)(C)C.C([O-])(O)=O.[Na+]>CO>[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](/[CH:17]=[CH:18]/[C:19]1[CH:20]=[CH:21][C:22]([CH:25]([CH2:26][CH2:27][N:28]2[CH2:33][C@@H:32]3[CH2:34][C@H:29]2[CH2:30][O:31]3)[C:35]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([Br:43])=[CH:39][CH:38]=2)=[O:44])=[CH:23][CH:24]=1)=[O:45]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68556317HCID 68556317, compound

Product 1

HCID 68556702HCID 68556702, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrochloric acid in methanol (1.25 M, 5 mL) was added to the (E)-[2-(3-{4-[1-(4-bromo-phenylcarbamoyl)-3-({1S,4S}-2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)-propyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester residue, the mixture was stirred for about 4 h, and then NaHCO3 was added to the reaction system. After filtration of solids, the crude mixture was purified by preparative HPLC to obtain light yellow solid. MS: calc'd 575 (MH+), exp 575 (MH+). 1H NMR (d6-DMSO, 400 MHz), 10.25 (d, 1H, J=8.8 Hz), 9.40 (s, 1H), 7.59-7.45 (broad m, 9H), 7.39 (d, 1H, J=8.0 Hz), 6.94-6.85 (m, 2H), 6.75 (d, 1H, J=8.0 Hz), 6.58 (t, 1H, J=8.0 Hz), 4.95 (s, 1H), 4.31 (s, 1H), 3.85-3.78 (broad m, 2H), 3.47-3.42 (broad m, 2H), 2.78 (broad s, 1H), 2.43-2.20 (broad m, 3H), 1.78-1.54 (broad m, 3H).

Workup

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

Sources & evidence

ORD record
ord-b49907b221174047b4b82ec6630c89e0
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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