Dimethylamine → HCID 57563140, compound

HRID 1726184Notes

Reaction equation

C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]#[N:40])[CH:34]=2)[CH:11]2[CH2:16][CH2:15][N:14]([CH:17]([CH3:31])[CH2:18][CH2:19][NH:20][C:21]([C:23]3[C:28]([Cl:29])=[CH:27][N:26]=[CH:25][C:24]=3[Cl:30])=[O:22])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[CH3:42][NH:43][CH3:44]>>[Cl:29][C:28]1[CH:27]=[N:26][CH:25]=[C:24]([Cl:30])[C:23]=1[C:21]([NH:20][CH2:19][CH2:18][CH:17]([N:14]1[CH2:15][CH2:16][CH:11]([N:10]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]#[N:40])[CH:34]=2)[C:7]2[CH:8]=[CH:9][C:4]([C:3](=[O:2])[N:43]([CH3:44])[CH3:42])=[CH:5][CH:6]=2)[CH2:12][CH2:13]1)[CH3:31])=[O:22]

Participants

Reactant 2

HCID 674Dimethylamine

HCID 57562992HCID 57562992, compound

Product 1

HCID 57563140HCID 57563140, compoundYield 50%

Procedure

Using general procedure K with COMPOUND 107 (36 mg, 0.06 mmol) followed by general procedure E with the resulting acid and dimethylamine (2.0M in THF, 31 μL, 0.062 mmol) afforded COMPOUND 128 as a white solid (18 mg, 50% over 2 steps). 1H NMR (CDCl3) δ 0.96-1.25 (m, 2H), 1.29 (d, 3H, J=5.7 Hz), 1.54-1.58 (m, 1H), 1.71-1.80 (m, 3H), 2.17-2.25 (m, 1H), 2.56-2.64 (m, 1H), 2.81-2.95 (m, 3H), 3.03 (s, 6H), 3.33-3.40 (m, 1H), 3.70-3.87 (m, 2H), 3.92 (s, 2H), 6.51 (d, 2H, J=8.7 Hz), 7.26-7.28 (m, 2H), 7.46-7.55 (m, 4H), 8.47 (s, 2H), 8.76 (br s, 1H). 13C NMR (CDCl3) δ 13.81, 29.79, 30.85, 40.47, 43.94, 48.36, 52.30, 56.17, 60.52, 112.38, 112.61, 113.15, 119.26, 125.14, 129.54, 129.75, 129.84, 130.05, 131.11, 131.17, 141.47, 147.98, 149.42, 172.01. ES-MS m/z 607 (M+H). Anal. Calcd. for C32H36N6Cl2O2.0.6CH2Cl2: C, 59.46; H, 5.69; N, 12.76. Found. C, 59.52; H, 5.64; N, 12.41.

Sources & evidence

ORD record: ord-22693ba39fac402eb65c15851343a56e
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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