Diisopropylethylamine → HCID 178485620, compound

HRID 527915

Reaction equation

HRID 527915 reaction equation
[CH3:1][NH:2][C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]2[C:9]3[CH:16]=[CH:15][N:14]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:4]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:56]1[CH:60]=[C:59]([CH2:61][C:62]([OH:64])=O)[N:58]=[CH:57]1>C1COCC1>[NH:56]1[CH:60]=[C:59]([CH2:61][C:62]([N:2]([CH3:1])[C@@H:3]2[CH2:7][CH2:6][N:5]([C:8]3[C:9]4[CH:16]=[CH:15][N:14]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:10]=4[N:11]=[CH:12][N:13]=3)[CH2:4]2)=[O:64])[N:58]=[CH:57]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 96215Imidazole-4-acetic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66765875(R)-N-methyl-1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-amine

Product 1

HCID 178485620HCID 178485620, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)—N-methyl-1-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-amine (0.29 mmol), TBTU (0.35 mmol) and DIPEA (0.58 mmol) in THF was slowly added 2-(1H-imidazol-4-yl)acetic acid (0.29 mmol). The mixture was stirred at room temperature overnight, then concentrated, diluted with water, and extracted with EtOAc. The combined extracts were dried, filtered and concentrated. The residue was purified by flash chromatography to give the title compound.

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. customThe combined extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-2d213c21ff16469e87bc93c1891701c0
Source dataset
uspto-grants-2016_05
Patent number
US09346810B2

Linked notes

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