Methylamine → HCID 70008308, compound

HRID 1266030Notes

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][NH2:25]>>[F:1][C:2]1[C:3]2[C:4]3[N:5]([C:13]([C:16]4[CH:17]=[CH:18][C:19]([CH2:20][NH:25][CH3:24])=[CH:22][CH:23]=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 6329Methylamine

HCID 178519439HCID 178519439, compound

Product 1

HCID 70008308HCID 70008308, compound

Procedure

The title compound was prepared following the procedure described in Example 32 from aldehyde 97a and methylamine (2M/MeOH) to give 0.069 g (42%) of a white solid: mp=204-208° C. (dec); Rf=0.03 (7% methanolic ammonia/CHCl3); IR (KBr) 1655, 1609, 1470, 1437 cm−1; 1H NMR (DMSO-d6) δ 2.30 (s, 3H), 3.54-3.55 (m, 2H), 3.75 (s, 2H), 4.45-4.46 (m, 2H), 7.52 (d, 2H, J=8.2 Hz), 7.57-7.61 (m, 1H), 7.73-7.76 (m, 1H), 7.80 (d, 2H, J=8.2 Hz), 8.59-8.63 (m, 1H). HRMS calcd for C18H17N4OF 324.1386 (M+), found 324.1378. Anal. (C18H17N4OF.0.3H2O) C, H, N.

Sources & evidence

ORD record: ord-dab9f4f87ab44955b35c0e554bf5064c
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548494B1

Reaction notes

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