3-(Morpholinomethyl)benzaldehyde → HCID 178513989, compound

HRID 591928Notes

Reaction equation

HRID 591928 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[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](C3C=CC(CN4CCOCC4)=CC=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.[N:62]1([CH2:68][C:69]2[CH:70]=[C:71]([CH:74]=[CH:75][CH:76]=2)C=O)[CH2:67][CH2:66][O:65][CH2:64][CH2:63]1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[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:71]3[CH:74]=[CH:75][CH:76]=[C:69]([CH2:68][N:62]4[CH2:67][CH2:66][O:65][CH2:64][CH2:63]4)[CH:70]=3)[NH:15][C:12]2=[N:13][CH:14]=1

Participants

4

Reactant 3

HCID 71646033-(Morpholinomethyl)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 178513989HCID 178513989, compoundYield 77%

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-Morpholin-4-ylmethyl-benzaldehyde were reacted to produce the title compound (77%). 1H NMR (d-chloroform): 8.78 (d, J=8 Hz, 1H), 8.20 (m, 1H), 8.09 (s, 1H), 7.85 (s, 1H), 7.63 (m, 2H), 6.42-6.50 (m, 2H), 6.01 (s, 1H), 5.61 (s, 1H), 5.38 (t, J=8 Hz, 1H), 4.37 (d, J=13 Hz, 1H), 4.27 (d, J=13 Hz, 1H), 3.99 (m, 4H), 3.53 (m, 2H), 3.18 (s, 1H), 3.05 (m, 1H), 3.04 (s, 1H), 2.70 (d, J=8 Hz, 1H), 2.32 (d, J=9 Hz, 1H), 1.68 (d, J=9 Hz, 1H). MS: 480.09 (M+H). HPLC retention time: 1.81 minutes (G Method).

Sources & evidence

ORD record
ord-d21b656253e145c9bc8c15f761392158
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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