Water → 4-({[3,5-Dicyano-6-(3-hydroxyazetidin-1-yl)-4-phenylpyridin-2-yl]sulfanyl}methyl)-N-methylpyridine-2-carboxamide

HRID 714481Notes

Reaction equation

HRID 714481 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:3]=1[C:28]#[N:29].Cl.[NH:31]1[CH2:34][CH:33]([OH:35])[CH2:32]1.C(N(CC)CC)C.O>O1CCCC1>[C:20]([C:5]1[C:6]([S:8][CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]([NH:18][CH3:19])=[O:17])[CH:11]=2)=[N:7][C:2]([N:31]2[CH2:34][CH:33]([OH:35])[CH2:32]2)=[C:3]([C:28]#[N:29])[C:4]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)#[N:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 27592903-Hydroxyazetidine hydrochlorideHCID 582973474-{[(6-Chloro-3,5-dicyano-4-phenylpyridin-2-yl)thio]methyl}-N-methylpyridine-2-carboxamide

Product 1

HCID 565921814-({[3,5-Dicyano-6-(3-hydroxyazetidin-1-yl)-4-phenylpyridin-2-yl]sulfanyl}methyl)-N-methylpyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

50 mg (0.12 mmol) of 4-{[(6-chloro-3,5-dicyano-4-phenylpyridin-2-yl)sulfanyl]methyl}-N-methylpyridine-2-carboxamide Example 75A, 19.6 mg (0.18 mmol) of azetidin-3-ol hydrochloride and 36.2 mg (0.36 mmol) of triethylamine were dissolved in 1 ml of tetrahydrofuran, and the mixture was stirred at RT for 1 h. Water and tetrahydrofuran were added to the reaction mixture until a solution had formed. The solution was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid).

Workup

  1. customhad formed
  2. customThe solution was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-e7307b1cdf3c4898ba71d75292682fbc
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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