1,2-Dichloroethane → 3-(6-amino-pyridin-3-yl)-N-(3-cyano-1H-indol-2-ylmethyl)-N-methyl-acrylamide

HRID 1362354Notes

Reaction equation

HRID 1362354 reaction equation
C(Cl)CCl.[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)=[CH:8][CH:7]=1.[CH3:17][NH:18][CH2:19][C:20]1[NH:21][C:22]2[C:27]([C:28]=1[C:29]#[N:30])=[CH:26][CH:25]=[CH:24][CH:23]=2.C1C=CC2N(O)N=NC=2C=1.O.CCN(C(C)C)C(C)C>CN(C=O)C.O>[NH2:5][C:6]1[N:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]([N:18]([CH2:19][C:20]2[NH:21][C:22]3[C:27]([C:28]=2[C:29]#[N:30])=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:17])=[O:16])=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 592775892-methylaminomethyl-1H-indole-3-carbonitrile

Product 1

HCID 669672553-(6-amino-pyridin-3-yl)-N-(3-cyano-1H-indol-2-ylmethyl)-N-methyl-acrylamideYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDC (250 mg, 1.3 mmol) was added to a solution of (E)-3-(6-Amino-pyridin-3-yl)-acrylic acid (172 mg, 1.05 mmol), 2-methylaminomethyl-1H-indole-3-carbonitrile (186 mg, 1.0 mmol), HOBt H2O (135 mg, 1.0 mmol) and DIPEA (510 μL, 3.0 mmol) in dry DMF (4 mL). After 3 d of stirring, the mixture was diluted with water (50 mL) at 10° C. The resulting precipitate was filtered, washed with water and dried to afford the title compound (277 mg, 84%). 1H NMR (300 MHz, DMSO-d6, δ): 12.1 (m, 1H), 8.16 (s, 1H), 7.84 (s, 1H), 7.5 (m, 3H), 7.2 (m, 2H), 6.97 (m, 1H), 6.44 (s, 2H), 5.08 and 4.88 (rotamers, 2s, 2H), 3.22 and 2.96 (rotamers, 2s, 3H). MS (ESI): m/e 332 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-7b1b1390941f4a38b4784c966b49a428
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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