Acetic Acid → HCID 73504720, compound

HRID 1478565Notes

Reaction equation

HRID 1478565 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@@H:17]4[CH2:22][N:21]([C:23]5[N:28]=[CH:27][C:26]([C:29]6[CH:36]=[CH:35][C:32](C=O)=[CH:31][CH:30]=6)=[CH:25][N:24]=5)[CH2:20][CH2:19][O:18]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1.[C:43](O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@H:17]4[O:18][CH2:19][CH2:20][N:21]([C:23]5[N:28]=[CH:27][C:26]([C:29]6[CH:36]=[CH:35][C:32]([CH2:43][N:37]7[CH2:42][CH2:41][O:40][CH2:39][CH2:38]7)=[CH:31][CH:30]=6)=[CH:25][N:24]=5)[CH2:22]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8083MorpholineHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 118364860HCID 118364860, compound

Product 1

HCID 73504720HCID 73504720, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-4-(2-(2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholino)pyrimidin-5-yl)benzaldehyde 40 mg (0.08 mmol) was dissolved in methylene chloride 3 ml, and morpholine 14 μl (0.17 mmol), acetic acid 5.7 μl (0.09 mmol), and NaBH(OAc)3 26.5 mg (0.12 mmol) were added and then charged with nitrogen, followed by stirring at room temperature for 18 hours. After the reaction, the reaction mixture was cooled and adjusted to pH 8 with K2CO3(aq.), followed by extraction with MC and water, and the organic layer was dried over MgSO4. Column chromatography (methylene chloride:methanol=20:1) gave a product 18.7 mg (41%).

Workup

  1. additioncharged with nitrogen
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled
  4. extractionfollowed by extraction with MC and water
  5. dry with materialthe organic layer was dried over MgSO4

Sources & evidence

ORD record
ord-2e63519c0a5347879da070d54f4484df
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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