Hydrochloric Acid → (E)-N-Methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide hydrochloride

HRID 1879973Notes

Reaction equation

HRID 1879973 reaction equation
[CH3:1][N:2]([CH2:18][C:19]1[O:20][C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=2[C:23]=1[CH3:24])[C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:16]=[N:15][C:9]2[NH:10][CH2:11][CH2:12][NH:13][CH2:14][C:8]=2[CH:7]=1.[ClH:29]>C(Cl)Cl.CCOCC>[ClH:29].[CH3:1][N:2]([CH2:18][C:19]1[O:20][C:21]2[CH:28]=[CH:27][CH:26]=[CH:25][C:22]=2[C:23]=1[CH3:24])[C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:16]=[N:15][C:9]2[NH:10][CH2:11][CH2:12][NH:13][CH2:14][C:8]=2[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 45487682(E)-N-Methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide

Product 1

HCID 68411606(E)-N-Methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide hydrochlorideYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of (E)-N-methyl-N-(3-methylbenzofuran-2-ylmethyl)-3-(2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylamide (0.21 g, 0.56 mmol) in CH2Cl2 (5 mL) was treated with anhydrous HCl (0.56 mL of a 1.0 M solution in Et2O, 0.56 mmol). After stirring for 5 min, the mixture was diluted with Et2O (50 mL), allowed to stir for 30 min and sonicated for 5 min. The solid was isolated by filtration, washed with Et2O, and dried under vacuum at 50° C. for 4 days to give the title compound (0.22 g, 97%) as an off-white powder and as a mixture of amide rotamers: 1H NMR (300 MHz, DMSO-d6) δ 9.66 (br s, 2H), 8.36-8.33 (m, 1H), 8.14 (s, 1H), 7.58-7.07 (m, 7H), 4.98-4.79 (m, 2H), 4.26 (s, 2H), 3.51 (s, 2H), 3.33 (s, 2H), 3.17-2.91 (m, 3H), 2.27 (s, 3H); MS (ESI) m/e 377 (M+H)+.

Workup

  1. stirringto stir for 30 min
  2. customsonicated for 5 min
  3. customThe solid was isolated by filtration
  4. washwashed with Et2O
  5. customdried under vacuum at 50° C. for 4 days

Sources & evidence

ORD record
ord-d088ce5c4df24296ab1a7dfaff3d8248
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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