2-[Butyl(methyl)amino]-6-chloroisonicotinic acid → 2-[butyl(methyl)amino]-6-chloro-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}isonicotinamide

HRID 349028Notes

Reaction equation

HRID 349028 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:37]=[C:38]([F:40])[CH:39]=1)[CH2:5][C@H:6]([NH:20]C(C1C=C(C)N=C(N(CCC)CCC)N=1)=O)[C@H:7]([OH:19])[CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH3:18])[CH:12]=1.[CH2:41]([N:45]([CH3:56])[C:46]1[CH:47]=[C:48]([CH:52]=[C:53]([Cl:55])[N:54]=1)[C:49]([OH:51])=O)[CH2:42][CH2:43][CH3:44]>>[CH2:41]([N:45]([CH3:56])[C:46]1[CH:47]=[C:48]([CH:52]=[C:53]([Cl:55])[N:54]=1)[C:49]([NH:20][C@@H:6]([CH2:5][C:4]1[CH:37]=[C:38]([F:40])[CH:39]=[C:2]([F:1])[CH:3]=1)[C@H:7]([OH:19])[CH2:8][NH:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH3:18])[CH:12]=1)=[O:51])[CH2:42][CH2:43][CH3:44]

Participants

3

Reactant 2

HCID 210854302-[Butyl(methyl)amino]-6-chloroisonicotinic acidHCID 58802606N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-2-(dipropylamino)-6-methylpyrimidine-4-carboxamide

Product 1

HCID 588023102-[butyl(methyl)amino]-6-chloro-N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}isonicotinamide

Procedure

In the same manner as for N-{(1S,2R)-1-(3,5-difluorobenzyl)-3-[(3-ethylbenzyl)amino]-2-hydroxypropyl}-2-(dipropylamino)-6-methylpyrimidine-4-carboxamide {EXAMPLE S-2435}, Step 3, 2-[butyl(methyl)amino]-6-chloroisonicotinic acid (0.15 g) was converted to 0.13 g of the title compound.

Sources & evidence

ORD record
ord-237353a11b53429480c011f3014c36e5
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Reaction notes

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