Dichloromethane → HCID 60169549, compound

HRID 536597

Reaction equation

HRID 536597 reaction equation
[C:1]([NH2:5])([CH3:4])(C)C.C(OC([N:13]1CC[C:16](=O)[CH2:15][C@H:14]1C(O)=O)=O)(C)(C)C.[CH3:23][C:24]1[CH:25]=[CH:26][C:27]([C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[C:28]([CH:32]=1)[C:29]([OH:31])=O.CC[N:41]([CH:45]([CH3:47])C)[CH:42]([CH3:44])[CH3:43].C(P1(=O)OP(CCC)(=O)OP([CH2:62][CH2:63][CH3:64])(=O)O1)CC.C(Cl)[Cl:67]>>[Cl:67][C:15]1[CH:16]=[CH:4][C:1]([NH:5][CH2:44][C@H:42]2[N:41]([C:29]([C:28]3[CH:32]=[C:24]([CH3:23])[CH:25]=[CH:26][C:27]=3[C:33]3[N:38]=[CH:37][CH:36]=[CH:35][N:34]=3)=[O:31])[CH2:45][CH2:47][C:62]3([CH2:63][CH2:64]3)[CH2:43]2)=[N:13][CH:14]=1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 445172645-Methyl-2-(pyrimidin-2-yl)benzoic acidHCID 66848353(S)-1-Boc-4-oxopiperidine-2-carboxylic acid tert-butylamine salt

Product 1

HCID 60169549HCID 60169549, compound

Procedure

Alternatively Compound 13 was obtained by the following procedure: 5-methyl-2-(pyrimidin-2-yl)benzoic acid (428 mg, 2 mmol; prepared according to WO 2008147518), intermediate 34 (500 mg, 2 mmol) and DIPEA (0.65 ml) were dissolved in DCM (5 ml) at 0° C., then T3P (50% in DCM, 1.5 g) was added. The mixture is stirred at reflux for 8 hours then at RT overnight. The reaction was washed with NaOH 1M and water, dried (Na2SO4) and evaporated. The crude was purified by silica gel column chromatography (DCM to DCM/MeOH=95/05). 180 mg of the desired compound were isolated.

Workup

  1. temperatureat reflux for 8 hours
  2. customat RT
  3. customovernight
  4. washThe reaction was washed with NaOH 1M and water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe crude was purified by silica gel column chromatography (DCM to DCM/MeOH=95/05)

Sources & evidence

ORD record
ord-b24d643e62b54fb8942e4316b1d777d7
Source dataset
uspto-grants-2014_10
Patent number
US08859608B2

Linked notes

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