Dimethylamine → HCID 70006868, compound

HRID 1266031Notes

Reaction equation

[F:1][C:2]1[C:3]2[C:4]3[N:5]([C:13]([C:16]4[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=4)=[N:14][CH:15]=2)[CH2:6][CH2:7][C:8]=3[NH:9][C:10](=[O:12])[CH:11]=1.[CH3:24][NH:25][CH3:26]>>[F:1][C:2]1[C:3]2[C:4]3[N:5]([C:13]([C:16]4[CH:23]=[CH:22][C:19]([CH2:20][N:25]([CH3:26])[CH3:24])=[CH:18][CH:17]=4)=[N:14][CH:15]=2)[CH2:6][CH2:7][C:8]=3[NH:9][C:10](=[O:12])[CH:11]=1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 178519439HCID 178519439, compound

Product 1

HCID 70006868HCID 70006868, compound

Procedure

The title compound was prepared following the procedure described in Example 32 from aldehyde 97a and dimethylamine (2M/MeOH) to give 0.10 g (60%) of a white solid: mp=240° C. (dec); Rf=0.08 (7% methanolic ammonia/CHCl3); IR (KBr) 1669, 1607, 1487, 1458 cm−1; 1H NMR (DMSO-d6) δ 2.20 (s, 6H), 3.51 (s, 2H), 3.54-3.55 (m, 2H), 4.45-4.47 (m, 2H), 7.50 (d, 2H, J=8.2 Hz), 7.57-7.61 (m, 1H), 7.73-7.76 (m, 1H), 7.82 (d, 2H, J=8.2 Hz), 8.59-8.63 (m, 1H). HRMS calcd for C19H19N4OF 338.1543 (M+), found 338.1558. Anal. (C19H19N4OF0.2H2O) C, H, N. found 412.2124. Anal. (C25H25N5O.0.5 H2O, 3.5 TFA) C, H, N.

Sources & evidence

ORD record: ord-16430913d6f248dcb065c15bf50960ff
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548494B1

Reaction notes

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