Acetic Acid → HCID 178521048, compound

HRID 931320Notes

Reaction equation

HRID 931320 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2([C:10](=[NH:14])OCC)[CH2:9][CH2:8]2)[CH:6]=1.[S].C(O)(=O)C.C(N(CC)CC)C.N[C:28]1[C:33]([NH2:34])=[CH:32][N:31]=[C:30]([N:35]2[CH2:40][CH2:39][O:38][C@@H:37]([C:41]([N:43]3[CH2:47][CH2:46][CH2:45][CH2:44]3)=[O:42])[CH2:36]2)[N:29]=1>>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2([C:10]3[NH:14][C:32]4[C:33]([N:34]=3)=[CH:28][N:29]=[C:30]([N:35]3[CH2:40][CH2:39][O:38][C@@H:37]([C:41]([N:43]5[CH2:47][CH2:46][CH2:45][CH2:44]5)=[O:42])[CH2:36]3)[N:31]=4)[CH2:8][CH2:9]2)[CH:6]=1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5362487SulfurHCID 89853939(R)-(4-(4,5-Diaminopyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanoneHCID 117966385ethyl 1-(4-chloro-1H-pyrazol-1-yl)cyclopropanecarbimidate

Product 1

HCID 178521048HCID 178521048, compound

Conditions

Temperature
100 °C

Procedure

Ethyl 1-(4-chloro-1H-pyrazol-1-yl)cyclopropanecarbimidate (0.13 g, 0.46 mmol), sulfur (15 mg), acetic acid (0.53 mL, 9.3 mmol) and triethylamine (0.39 mL, 2.79 mmol) were added to the filtrate containing (R)-(4-(4,5-diaminopyrimidin-2-yl)morpholin-2-yl)(pyrrolidin-1-yl)methanone, prepared in the previous step, at room temperature. The reaction mixture was heated to 100° C. for 24 h. The solvent was removed under reduced pressure and the resulting crude material was purified via preparative TLC to afford the title compound (13 mg). MS (ES+APCI) (M+H) 443.0; LCMS retention time 4.485 min (Method T1).

Workup

  1. customprepared in the previous step, at room temperature
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting crude material was purified via preparative TLC

Sources & evidence

ORD record
ord-0fc590a173bb4398aee2c52c9be96340
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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