Hydrochloric Acid → N-[4-(7-amino-4-{[(dimethylamino)methylene]amino}thieno[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-indole-2-carboxamide

HRID 1270964Notes

Reaction equation

HRID 1270964 reaction equation
[CH3:1][N:2]([CH:4]=[N:5][C:6]1[C:11]2[C:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]4[N:25]([CH3:33])[C:26]5[C:31]([CH:32]=4)=[CH:30][CH:29]=[CH:28][CH:27]=5)=[O:23])=[C:17]([O:34][CH3:35])[CH:16]=3)=[CH:13][S:14][C:10]=2[C:9]([N:36]=C(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:8][N:7]=1)[CH3:3].Cl>O1CCCC1.CO.ClCCl>[NH2:36][C:9]1[C:10]2[S:14][CH:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]4[N:25]([CH3:33])[C:26]5[C:31]([CH:32]=4)=[CH:30][CH:29]=[CH:28][CH:27]=5)=[O:23])=[C:17]([O:34][CH3:35])[CH:16]=3)[C:11]=2[C:6]([N:5]=[CH:4][N:2]([CH3:3])[CH3:1])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18451392N-(4-{4-{[(dimethylamino)methylene]amino}-7-[(diphenylmethylene)amino]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide

Product 1

HCID 18451398N-[4-(7-amino-4-{[(dimethylamino)methylene]amino}thieno[3,2-c]pyridin-3-yl)-2-methoxyphenyl]-1-methyl-1H-indole-2-carboxamideYield 96%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

N-(4-{4-{[(dimethylamino)methylene]amino}-7-[(diphenylmethylene)amino]thieno[3,2-c]pyridin-3-yl}-2-methoxyphenyl)-1-methyl-1H-indole-2-carboxamide (0.117 g, 0.177 mmol) was dissolved in tetrahydrofuran (5 mL), and aqueous hydrochloric acid (1 M, 0.24 mL) was added, and the mixture was stirred at ambient temperature for 12 h. The mixture was diluted with methanol/dichloromethane (1:19, 50 mL) the resulting solution was extracted with aqueous sodium bicarbonate (1 M, 10 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated. Purification of the residue by flash column chromatography on silica gel which had been deactivated with triethylamine (10% by volume of silica gel used) using methanol/dichloromethane (1:19) as the mobile phase afforded the title compound (0.085 g, 0.17 mmol) as a tan powder: 1H NMR (DMSO-d6, 400 MHz) δ 9.40 (s, 1H), 8.13 (s, 1H), 7.79 (d, 1H), 7.70 (d, 1H), 7.58 (d, 1H), 7.56 (s, 1H), 7.49 (s, 1H), 7.33 (m, 2H), 7.15 (t, 1H), 7.06 (m, 1H), 7.01 (d, 1H), 5.07 (br, 2H), 4.04 (s, 3H), 3.88 (s, 3H), 2.94 (s, 3H), 2.47 (s, 3H); MS: (MH)+ 499.

Workup

  1. extractionwas extracted with aqueous sodium bicarbonate (1 M, 10 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue by flash column chromatography on silica gel which

Sources & evidence

ORD record
ord-e2ed07c312ab479180c322add2016a4a
Source dataset
uspto-grants-2007_04
Patent number
US07202363B2

Reaction notes

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