Hydrochloric Acid → HCID 16659985, compound

HRID 2097077Notes

Reaction equation

HRID 2097077 reaction equation
[CH3:1][C:2]1([CH3:31])[C:8](=[O:9])[NH:7][C:6]2[N:10]=[CH:11][C:12](/[CH:14]=[CH:15]/[C:16]([N:18]([CH3:30])[CH2:19][C:20]3[N:21]([CH3:29])[C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1.[ClH:32]>C(Cl)Cl.CCOCC>[ClH:32].[CH3:1][C:2]1([CH3:31])[C:8](=[O:9])[NH:7][C:6]2[N:10]=[CH:11][C:12](/[CH:14]=[CH:15]/[C:16]([N:18]([CH3:30])[CH2:19][C:20]3[N:21]([CH3:29])[C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:17])=[CH:13][C:5]=2[CH2:4][NH:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 16659986HCID 16659986, compound

Product 1

HCID 16659985HCID 16659985, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A suspension of (E)-3-(3,3-dimethyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide (0.15 g, 0.36 mmol) in CH2Cl2 (5 mL) was treated with anhydrous HCl (0.36 mL of a 1.0 M solution in Et2O, 0.36 mmol). After stirring for 10 min, the mixture was diluted with Et2O (50 mL) and then stirred for 1.5 h. The solid was isolated by filtration, washed with Et2O, and dried under vacuum at 50° C. for 3 d to give the title compound (0.14 g, 83%) as a tan powder and as a mixture of amide rotamers: 1H NMR (500 MHz, DMSO-d6) δ 10.90-10.87 (m, 1H), 10.54 (br s, 2H), 8.66-8.63 (m, 1H), 8.39-8.33 (s, 1H), 7.62-7.59 (m, 1H), 7.51-7.32 (m, 3H), 7.14-7.11 (m, 1H), 7.03-6.99 (m, 1H), 6.43-6.19 (m, 1H), 5.07-4.86 (m, 2H), 4.40-4.35 (m, 2H), 3.74-3.69 (m, 3H), 3.13-3.00 (m, 3H), 1.63-1.59 (m, 6H); MS (ESI) m/e 418 (M+H)+.

Workup

  1. stirringstirred for 1.5 h
  2. customThe solid was isolated by filtration
  3. washwashed with Et2O
  4. customdried under vacuum at 50° C. for 3 d

Sources & evidence

ORD record
ord-ee6a4d40a869464d906ee8c47e85e95e
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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