methyl((1-methyl-1H-indol-2-yl)methyl)amine → HCID 10433701, compound

HRID 1362212Notes

Reaction equation

HRID 1362212 reaction equation
Cl.[CH3:2][N:3]([CH3:22])[CH2:4][CH2:5][N:6]1[CH2:11][C:10]2[CH:12]=[C:13](/[CH:16]=[CH:17]/[C:18]([OH:20])=O)[CH:14]=[N:15][C:9]=2[NH:8][C:7]1=[O:21].Cl.[CH3:24][N:25]1[CH2:31][C:30]2[CH:32]=[C:33](/[CH:36]=[CH:37]/[C:38](O)=O)C=N[C:29]=2[NH:28][C:27](=O)[CH2:26]1.CNCC1N(C)C2C(C=1)=CC=CC=2.CNCC1C=CC2C(=CC=CC=2)C=1CCC>>[CH3:22][N:3]([CH3:2])[CH2:4][CH2:5][N:6]1[CH2:11][C:10]2[CH:12]=[C:13](/[CH:16]=[CH:17]/[C:18]([N:28]([CH3:29])[CH2:27][C:26]3[N:25]([CH3:24])[C:31]4[C:37]([CH:38]=3)=[CH:36][CH:33]=[CH:32][CH:30]=4)=[O:20])[CH:14]=[N:15][C:9]=2[NH:8][C:7]1=[O:21]

Participants

5

Reactant 4

HCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 59456959Methyl-(1-propyl-naphthalen-2-ylmethyl)amineHCID 66966197(E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochlorideHCID 66966913HCID 66966913, compound

Product 1

HCID 10433701HCID 10433701, compoundYield 22%

Procedure

According to the procedure of Example 1 (a), except substituting (E)-3-[3-(2-dimethylamino-ethyl)-2-oxo-1,2,3,4-tetrahydro-pyrido[2,3-d]pyrimidin-6-yl]acrylic acid hydrochloride for the (E)-3-(4-methyl-2-oxo-2,3,4,5-tetrahydro-1H-pyrido[2,3-e][1,4]diazepin-7-yl)acrylic acid hydrochloride, and substituting methyl-(1-methyl-1H-indol-2-ylmethyl)amine for the methyl-(1-propyl-naphthalen-2-ylmethyl)amine, the title compound (40 mg, 22%) was prepared as a pale yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 9.98 (br s, 1H), 8.38-8.33 (m, 1H), 8.00-7.91 (m, 1H), 7.57-7.42 (m, 3H), 7.22-7.01 (m, 3H), 6.42-6.16 (m, 1H), 5.04-4.85 (m, 2H), 4.53-4.47 (m, 2H), 3.72-3.68 (m, 3H), 3.51-3.31 (m, 4H), 3.11-2.99 (m, 4H), 2.72-2.39 (m, 5H); MS (ESI) m/e 447 (M+H)+.

Sources & evidence

ORD record
ord-4b66fa91dda7429da30d01c500594553
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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