3-(Dimethylamino)benzaldehyde → HCID 178482748, compound

HRID 591926

Reaction equation

HRID 591926 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:10]([NH:31][C@@H:32]2[C@@H:37]3[CH2:38][C@@H:34]([CH:35]=[CH:36]3)[C@@H:33]2[C:39]([NH2:41])=[O:40])=[C:11]2[N:17]=[C:16]([C:18]3[CH:23]=C[C:21]([CH2:24][N:25]4[CH2:30]COC[CH2:26]4)=[CH:20][CH:19]=3)[NH:15][C:12]2=[N:13][CH:14]=1.NC1C(N)=C(N[C@@H]2[C@@H]3C[C@@H](C=C3)[C@@H]2C(N)=O)C(Cl)=CN=1.CN(C)C1C=C(C=CC=1)C=O>>[Cl:8][C:9]1[C:10]([NH:31][C@@H:32]2[C@@H:37]3[CH2:38][C@@H:34]([CH:35]=[CH:36]3)[C@@H:33]2[C:39]([NH2:41])=[O:40])=[C:11]2[N:17]=[C:16]([C:18]3[CH:19]=[CH:20][CH:21]=[C:24]([N:25]([CH3:30])[CH3:26])[CH:23]=3)[NH:15][C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 3

HCID 342883-(Dimethylamino)benzaldehydeHCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amideHCID 178513995HCID 178513995, compound

Product 1

HCID 178482748HCID 178482748, compoundYield 86%

Procedure

In the same fashion as for Compound III, (1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide and 3-Dimethylamino-benzaldehyde were reacted to produce the title compound (86%). 1H NMR (d-chloroform): 16.5 (br s, 1H), 8.37 (d, J=8 Hz, 1H), 7.83 (s, 1H), 7.72 (s, 1H), 7.61 (d, J=8 Hz, 1H), 7.45 (t, J=8 Hz, 1H), 7.06 (dd, J=2.8 Hz, 1H), 6.51 (m, 1H), 6.42 (m, 1H), 5.98 (m, 1H), 5.62 (m, 1H), 5.38 (t, J=8 Hz, 1H), 3.17 (s, 1H), 3.13 (s, 6H), 3.06 (s, 1H), 2.71 (d, J=8 Hz, 1H), 2.33 (d, J=8 Hz, 1H), 1.68 (d, J=8 Hz, 1H). MS: 424.04 (M+H). HPLC retention time: 2.06 minutes (G Method).

Sources & evidence

ORD record
ord-d8af996c8c594a8e8422abbf2592efe1
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Linked notes

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