Ammonia → HCID 9984149, compound

HRID 1362230Notes

Reaction equation

[O:1]=[C:2]1[CH2:6][CH2:5][C:4](=[O:7])[N:3]1[C:8]1[N:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]([N:18]([CH3:30])[CH2:19][C:20]2[S:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[C:21]=2[CH3:29])=[O:17])=[CH:10][CH:9]=1.O=C1CCC(=O)N1C1N=CC(/C=C/C([N:48]([CH3:60])[CH2:49][C:50]2[N:51]([CH3:59])[C:52]3C(C=2)=CC=CC=3)=O)=CC=1.CN1CCNCC1.N>>[CH3:30][N:18]([CH2:19][C:20]1[S:24][C:23]2[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=2[C:21]=1[CH3:29])[C:16](/[CH:15]=[CH:14]/[C:11]1[CH:10]=[CH:9][C:8]([NH:3][C:4](=[O:7])[CH2:5][CH2:6][C:2]([N:48]2[CH2:49][CH2:50][N:51]([CH3:59])[CH2:52][CH2:60]2)=[O:1])=[N:13][CH:12]=1)=[O:17]

Participants

Reactant 4

HCID 222Ammonia

HCID 531671-Methylpiperazine

HCID 59456977HCID 59456977, compound

HCID 66966975HCID 66966975, compound

Product 1

HCID 9984149HCID 9984149, compoundYield 51%

Procedure

According to the procedure of Example 110 except substituting 3-[6-(2,5-dioxo-pyrrolidin-1-yl)pyridin-3-yl]-N-methyl-N-(3-methyl-benzo[b]thiophen-2-ylmethyl)acrylamide for the (E)-3-[6-(2,5-dioxo-pyrrolidin-1-yl)-pyridin-3-yl]-N-methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide, and substituting 1-methylpiperazine for the ammonia, the title compound (0.53 g, 51%) was prepared as a light yellow solid: 1H NMR 300 MHz, DMSO-d6) δ 10.71 (br s, 1H), 8.74-8.61 (m, 1H), 8.22-8.15 (m, 1H), 8.13-8.05 (m, 1H), 7.91-7.85 (m, 1H), 7.78-7.71 (m, 1H), 7.60-7.50 (m, 1H), 7.39-7.33 (m, 3H), 5.15-4.88 (m, 2H), 3.75-3.61 (m, 2H), 3.38-3.28 (m, 3H), 3.19-3.10 (m, 2H), 3.05-2.75 (m, 4H), 2.71-2.51 (m, 7H), 2.41 (s, 3H); MS (ESI) m/e 520 (M+H)+.

Sources & evidence

ORD record: ord-ea6e0b52a26748269bf2b7b8df912896
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879872B2

Reaction notes

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