Tetrahydrofuran → HCID 118341209, compound

HRID 1753004Notes

Reaction equation

HRID 1753004 reaction equation
N[C:2]1[CH:7]=[C:6]([C:8]([C:10]2[C:14]3[CH:15]=[N:16][CH:17]=[CH:18][C:13]=3[N:12]([CH:19]3[CH2:22]O[CH2:20]3)[CH:11]=2)=[O:9])[CH:5]=[CH:4][N:3]=1.CC[N:25]([CH:29]([CH3:31])C)C(C)C.CCN=C=[N:36][CH2:37][CH2:38][CH2:39][N:40]([CH3:42])C.[CH:43]1C=CC2N(O)N=NC=2[CH:48]=1.C1C[O:56]CC1>C(O)(=O)C>[C:37]([C:38]1[CH:43]=[CH:48][C:42]([CH2:5][C:4]([NH:3][C:2]2[CH:31]=[CH:29][N:25]=[C:6]([C:8]([C:10]3[C:14]4[CH:15]=[N:16][CH:17]=[CH:18][C:13]=4[N:12]([CH:19]([CH3:20])[CH3:22])[CH:11]=3)=[O:9])[CH:7]=2)=[O:56])=[N:40][CH:39]=1)#[N:36]

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 90093723HCID 90093723, compound

Product 1

HCID 118341209HCID 118341209, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To a 0.2M solution of (2-Aminopyridin-4-yl)-(1-(oxetan-3-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl)methanone in THF (Preparation 24, 500 μL, 100 umol) was added a 0.26M solution of the appropriate acetic acid in THF (500 μL, (130 μmol), DIPEA (130 μmol), EDCI (130 μmol) followed by HOBt (100 μmol) and the reaction was stirred under microwave irradiation for 30 minutes at 70° C. The reaction mixture was concentrated in vacuo and purified using preparative HPLC to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified

Sources & evidence

ORD record
ord-b813e68bd4fa40088d5f0bf50cd00297
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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