2-Amino-2-methyl-1-propanol → HCID 60055735, compound

HRID 549026Notes

Reaction equation

HRID 549026 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[NH:24][C:16]2[N:17]=[CH:18][CH:19]=[C:20]([C:21]([OH:23])=O)[C:15]=2[CH:14]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:58][C:59]([CH3:63])([CH3:62])[CH2:60][OH:61]>CN(C)C=O>[OH:61][CH2:60][C:59]([NH:58][C:21]([C:20]1[C:15]2[CH:14]=[C:13]([C:6]3[C:5]4[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=4)[N:8]([CH3:12])[CH:7]=3)[NH:24][C:16]=2[N:17]=[CH:18][CH:19]=1)=[O:23])([CH3:63])[CH3:62]

Participants

6

Reactant 4

HCID 118072-Amino-2-methyl-1-propanolHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 224772042-(5-Methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

Product 1

HCID 60055735HCID 60055735, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2-(5-methoxy-1-methyl-1H-indol-3-yl)-1H-pyrrolo[2,3-b]pyridine-4 carboxylic acid [32 mg, Example 41(a)] in dry dimethylformamide (10 mL), under nitrogen, was treated with diisopropylethylamine (35 μL) followed by O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (38 mg). After stirring at room temperature for 1 hour this mixture was treated with a solution of 2-amino-2-methyl-1-propanol (10.5 μL) in dry dimethylformamide (1 mL) and stirring was then continued for a further 2 hours. The reaction mixture was evaporated and the residue was treated with saturated aqueous sodium bicarbonate solution (15 mL). This mixture was stirred for 1 hour and the resulting yellow solid was filtered, then washed well with water and then dried at 100° C. under vacuum to give the title compound (34 mg) as a yellow solid, m.p. 210-212° C.

Workup

  1. stirringstirring
  2. waitwas then continued for a further 2 hours
  3. customThe reaction mixture was evaporated
  4. additionthe residue was treated with saturated aqueous sodium bicarbonate solution (15 mL)
  5. stirringThis mixture was stirred for 1 hour
  6. filtrationthe resulting yellow solid was filtered
  7. washwashed well with water
  8. customdried at 100° C. under vacuum

Sources & evidence

ORD record
ord-d4cdf6acd04547ba8e8ec03bc01aa718
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

Loading…