1,4-Dioxane-2-carbaldehyde → HCID 66830368, compound

HRID 1040978Notes

Reaction equation

HRID 1040978 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]2[CH2:6][CH2:7][N:8]([C:11]([CH:13]3[CH2:18][O:17][CH2:16][CH2:15][O:14]3)=[O:12])[CH2:9][CH2:10][C:4]=2[CH:3]=1.O1CCOCC1C=O.Cl[C:30]1[N:35]=[C:34]([NH:36][C:37]2[C:46]([F:47])=[CH:45][CH:44]=[CH:43][C:38]=2[C:39]([NH:41][CH3:42])=[O:40])[C:33]([Cl:48])=[CH:32][N:31]=1>>[Cl:48][C:33]1[C:34]([NH:36][C:37]2[C:46]([F:47])=[CH:45][CH:44]=[CH:43][C:38]=2[C:39]([NH:41][CH3:42])=[O:40])=[N:35][C:30]([NH:1][C:2]2[CH:20]=[CH:19][C:5]3[CH2:6][CH2:7][N:8]([C:11]([CH:13]4[CH2:18][O:17][CH2:16][CH2:15][O:14]4)=[O:12])[CH2:9][CH2:10][C:4]=3[CH:3]=2)=[N:31][CH:32]=1

Participants

4

Reactant 3

HCID 201331821,4-Dioxane-2-carbaldehydeHCID 67264042HCID 67264042, compoundHCID 717421912-(2,5-Dichloropyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide

Product 1

HCID 66830368HCID 66830368, compound

Procedure

(7-Amino-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-1,4-dioxinan-2-yl-methanone, prepared in a similar manner as 7-Amino-8-methoxy-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-1,4-dioxinan-2-yl-methanone of Example 633b, was reacted with 2-(2,5-Dichloro-pyrimidin-4-ylamino)-3-fluoro-N-methyl-benzamide, in a similar manner as Example 601b, to yield desired product 2-{5-Chloro-2-[3-([1,4]dioxane-2-carbonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-ylamino]-pyrimidin-4-ylamino}-3-fluoro-N-methyl-benzamide as a lyophylate (31%); 1H NMR (400 MHz, DMSO-d6) δ 9.39 (d, J=9.23 Hz, 1H), 9.33 (s, 1H), 8.55 (m, 1H), 8.18 (s, 1H), 7.51-7.43 (m, 3H), 7.26 (s, 1H), 7.17 (m, 1H), 6.89 (m, 1H), 4.39 (m, 1H), 3.74-3.4 (bm, H2O+11H), 2.81 (m, 1H), 2.74 (d, J=4.55 Hz, 3H), 2.67 (m, 2H); MS (m/e) 555.14 (M+H).

Sources & evidence

ORD record
ord-5dedf79d40ed4e2285f05d12f9507ca8
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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