Isopropylamine → N-cyclopropyl-3-{[4-({5-[(isopropylamino)methyl]pyridin-2-yl}methoxy)benzoyl]amino}-4-methylbenzamide

HRID 403049Notes

Reaction equation

C1(N[C:5](=[O:32])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([NH:13][C:14](=[O:31])[C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29]O)=[CH:25][N:24]=4)=[CH:17][CH:16]=3)[CH:7]=2)CC1.[CH:33]([NH2:36])([CH3:35])[CH3:34]>>[CH:33]1([NH:36][C:5](=[O:32])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([NH:13][C:14](=[O:31])[C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([CH2:29][NH:13][CH:8]([CH3:9])[CH3:7])=[CH:25][N:24]=4)=[CH:19][CH:20]=3)[CH:7]=2)[CH2:35][CH2:34]1

Participants

Reactant 2

HCID 6363Isopropylamine

HCID 11304999HCID 11304999, compound

Product 1

HCID 11167366N-cyclopropyl-3-{[4-({5-[(isopropylamino)methyl]pyridin-2-yl}methoxy)benzoyl]amino}-4-methylbenzamide

Procedure

Using an analogous procedure to that described in Example 27, N-cyclopropyl-3-[(4-{[5-(hydroxymethyl)pyridin-2-yl]methoxy}benzoyl)amino]-4-methylbenzamide was oxidised and the resulting aldehyde reacted with isopropylamine to give the title compound; NMR Spectrum: (DMSOd6) 0.58 (m, 2H), 0.68 (m, 2H), 1.00 (d, 6H), 2.25 (s, 3H), 2.70 (m, 1H), 2.86 (m, 1H), 3.71 (s, 2H), 5.76 (s, 2H), 7.14 (d, 2H), 7.33 (d, 1H), 7.49 (d, 1H), 7.64 (m, 1H), 7.80 (m, 2H), 7.99 (d, 2H), 8.40 (d, 1H), 8.55 (s, 1H), 9.87 (s, 1H); Mass Spectrum: M+H+ 473.

Sources & evidence

ORD record: ord-69998553bd7a490ca651c143f68b5a4f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742124B2

Reaction notes

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