Diisopropylethylamine → 3-[5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-(pyrrolidin-3-ylamino)-pyrimidin-4-ylamino]-N-methoxy-4-methyl-benzamide

HRID 852035Notes

Reaction equation

HRID 852035 reaction equation
[C:1]([C:3]1[C:4]([NH:19][C:20]2[CH:21]=[C:22]([CH:28]=[CH:29][C:30]=2[CH3:31])[C:23]([NH:25][O:26][CH3:27])=[O:24])=[N:5][C:6](S(C)=O)=[N:7][C:8]=1[N:9]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:10])#[N:2].C([N:39]1[CH2:43][CH2:42][C@@H:41]([NH2:44])[CH2:40]1)(OC(C)(C)C)=O.CCN(C(C)C)C(C)C>O1CCOCC1>[C:1]([C:3]1[C:4]([NH:19][C:20]2[CH:21]=[C:22]([CH:28]=[CH:29][C:30]=2[CH3:31])[C:23]([NH:25][O:26][CH3:27])=[O:24])=[N:5][C:6]([NH:44][CH:41]2[CH2:42][CH2:43][NH:39][CH2:40]2)=[N:7][C:8]=1[N:9]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:10])#[N:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 589285033-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methanesulfinyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamide

Product 1

HCID 724659043-[5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-(pyrrolidin-3-ylamino)-pyrimidin-4-ylamino]-N-methoxy-4-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3-{5-Cyano-6-[(2,2-dimethyl-propyl)-methyl-amino]-2-methanesulfinyl-pyrimidin-4-ylamino}-N-methoxy-4-methyl-benzamide (33 mg) and 1-N-Boc-3-(R)-aminopyrrolidine (30 mg), DIEA (0.2 mL) and p-dioxane (2 mL) were heated in a sealed tube at 75° C. for overnight. After the removal of the solvent in vacuo, the product was purified by silica gel column chromatography and treated with TFA/DCM (1:1) in order to remove the Boc-group. The product was then converted to hydrochloride salt by treating it with hydrochloric acid (1 M in ether) (Yield: 20 mg). MS (m/z): 567 (M+H).

Workup

  1. customAfter the removal of the solvent in vacuo
  2. customthe product was purified by silica gel column chromatography
  3. additiontreated with TFA/DCM (1:1) in order
  4. customto remove the Boc-group
  5. additionby treating it with hydrochloric acid (1 M in ether) (Yield: 20 mg)

Sources & evidence

ORD record
ord-4215c799fc114dbe80a71fdb6b2e71ce
Source dataset
uspto-grants-2007_08
Patent number
US07253174B2

Reaction notes

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