Morpholin-2-ylmethanol → HCID 66604601, compound

HRID 2410709Notes

Reaction equation

HRID 2410709 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[O:26][CH3:27])[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[CH:12][C:11]([C:17]([OH:19])=O)=[CH:10][C:9]2=1)(=[O:3])[NH2:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:52]1[CH2:57][CH2:56][O:55][CH:54]([CH2:58][OH:59])[CH2:53]1>CN(C1C=CN=CC=1)C.CN(C=O)C>[OH:59][CH2:58][CH:54]1[O:55][CH2:56][CH2:57][N:52]([C:17]([C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[NH:15][C:16]2[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][C:6]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[CH:7][C:8]3=2)=[O:19])[CH2:53]1

Participants

6

Reactant 3

HCID 3497988Morpholin-2-ylmethanolHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66599388HCID 66599388, compound

Product 1

HCID 66604601HCID 66604601, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

8-Carbamoyl-6-(2-methoxyphenyl)-9H-carbazole-3-carboxylic acid (31.5 mg, 0.061 mmol), HATU (75 mg, 0.197 mmol), DMAP (25 mg, 0.205 mmol), morpholin-2-ylmethanol (35 mg, 0.299 mmol) and DMF (3 ml) were combined and stirred at room temperature for 18 hours. The reaction mixture was filtered through a 0.45 um Nylon filter and purified by prep HPLC chromatography (water/CH3CN/NH4OAc eluent system). Product containing fractions were collected and evaporated in SPEEDVAC®. 13.4 mg 6-(2-(hydroxymethyl)morpholine-4-carbonyl)-3-(2-methoxyphenyl)-9H-carbazole-1-carboxamide were isolated as an off-white solid. MS (ESI) m/z 460 [M+H]. 1H NMR (CD3OD) δ ppm 8.45 (d, 1H, J=1.5), 8.27 (bs, 1H), 8.09 (d, 1H, J=1.5), 7.71 (d, 1H, J=8.6), 7.56 (dd, 1H, J=8.4, 1.7), 7.47 (dd, 1H, J=7.5, 1.7), 7.37 (dt, 1H, J˜8, ˜8, 1.7), 7.14 (d, 1H, J=8.5), 7.09 (dt, 1H, J=0.9, 7.5, 7.5), 4.05-3.90 (b, 2H), 3.86 (s, 3H), 3.70-3.55 (b, 4H), 3.5-3.0 (b, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through a 0.45 um Nylon
  2. filtrationfilter
  3. custompurified by prep HPLC chromatography (water/CH3CN/NH4OAc eluent system)
  4. additionProduct containing fractions
  5. customwere collected
  6. customevaporated in SPEEDVAC®

Sources & evidence

ORD record
ord-63feec3a8e4448f798a38956e96cc5ce
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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