Methylamine → HCID 69309525, compound

HRID 1947048Notes

Reaction equation

HRID 1947048 reaction equation
[S:1]([CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]2[CH2:30][CH2:29][CH:28]([C:31]([OH:33])=O)[CH2:27][CH2:26]2)[N:19]=1)(=[O:4])(=[O:3])[NH2:2].F[P-](F)(F)(F)(F)F.[N:41]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:45]2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.NC>C1COCC1.O>[CH3:45][NH:41][C:31]([CH:28]1[CH2:27][CH2:26][CH:25]([NH:24][C:20]2[N:19]=[C:18]([N:13]3[C:14]4[C:10](=[C:9]([O:8][CH2:7][CH2:6][CH2:5][S:1](=[O:3])(=[O:4])[NH2:2])[CH:17]=[CH:16][CH:15]=4)[CH:11]=[CH:12]3)[CH:23]=[CH:22][N:21]=2)[CH2:30][CH2:29]1)=[O:33]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 693071564-{4-[4-(3-Sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclo-hexanecarboxylic acid

Product 1

HCID 69309525HCID 69309525, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-{4-[4-(3-Sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexane-carboxylic acid (75 mg, 0.158 mmol), BOP (105.08 mg, 0.238 mmol), DIEA (55 μL, 0.317 mmol), and H2NMe (0.120 μL, 20% soln. in THF, 0.238 mmol) were combined in THF and allowed to stir at RT overnight. Water was then added to the reaction mixture and the mixture sonicated, and the solid filtered, washed with water, dried and recrystallized to yield 4-{4-[4-(3-sulfamoyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexanecarboxylic acid methylamide (Compound 319, 53.3 mg, 69.3%).

Workup

  1. customthe mixture sonicated
  2. filtrationthe solid filtered
  3. washwashed with water
  4. customdried
  5. customrecrystallized

Sources & evidence

ORD record
ord-1c8b0d238962442d91d8cbc14e64c87a
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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