Trimethylamine → HCID 16041606, compound

HRID 418621Notes

Reaction equation

[Cl:1][CH2:2][CH2:3][N:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[O:22][C:23]3[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:41])[CH2:31][C:32]([NH:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:33])=[CH:25][C:24]=3[F:42])[CH:14]=2)=[CH:9][CH:8]=1)[CH3:5].[N:43]([CH3:46])([CH3:45])[CH3:44]>COCCOC>[Cl-:1].[F:42][C:24]1[CH:25]=[C:26]([NH:29][C:30](=[O:41])[CH2:31][C:32](=[O:33])[NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:27]=[CH:28][C:23]=1[O:22][C:19]1[CH:18]=[CH:17][N:16]=[C:15]2[CH:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([CH2:6][N:4]([CH3:5])[CH2:3][CH2:2][N+:43]([CH3:46])([CH3:45])[CH3:44])=[CH:8][CH:9]=3)[S:21][C:20]=12

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 88 (80 mg, 0.133 mmol) in DME (1 mL) was added NMe3 (15.7 mg, 2 eq, 0.27 mmol) and the reaction mixture was heated to 100° C. in a sealed tube for an hour. The mixture was cooled to RT and concentrated. Purification (Gilson, 45 mins, 40% MeOH in water to 80% MeOH in water) afforded title compound 84 (20 mg, 9% yield). 1H NMR (DMSO-d6) δ (ppm): 10.85 (s, 1H), 10.41 (s, 1H), 8.47 (m, 2H), 8.05 (s, 1H), 7.85 (m, 3H), 7.59 (m, 2H), 7.42 (m, 5H), 7.32 (m, 2H), 7.05 (t, J=7.43 Hz, 1H), 6.63 (d, J=5.67, 1H), 3.60 (s, 2H), 3.51 (m, 2H), 3.1 (s, 9H), 2.81 (m, 2H), 2.20 (s, 3H). MS (m/z) 626.1 (M+H).

Workup

temperatureThe mixture was cooled to RT
concentrationconcentrated
customPurification (Gilson, 45 mins, 40% MeOH in water to 80% MeOH in water)

Sources & evidence

ORD record: ord-45b6efcd64314d18a2f268eb59d7b00f
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093264B2

Reaction notes

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