Ethyl isocyanate → HCID 178465274, compound

HRID 2279153Notes

Reaction equation

HRID 2279153 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:27])[CH:5]=[CH:6][C:7]=1[C:8]1[N:13]=[C:12]2[NH:14][N:15]=[C:16]([CH3:17])[C:11]2=[C:10]([CH2:18][N:19]2[CH2:25][CH2:24][CH2:23][NH:22][CH:21]([CH3:26])[CH2:20]2)[CH:9]=1.C1COCC1.[CH2:33]([N:35]=[C:36]=[O:37])[CH3:34].CCN(C(C)C)C(C)C>O>[CH2:33]([NH:35][C:36]([N:22]1[CH2:23][CH2:24][CH2:25][N:19]([CH2:18][C:10]2[CH:9]=[C:8]([C:7]3[CH:6]=[CH:5][C:4]([OH:27])=[CH:3][C:2]=3[F:1])[N:13]=[C:12]3[NH:14][N:15]=[C:16]([CH3:17])[C:11]=23)[CH2:20][CH:21]1[CH3:26])=[O:37])[CH3:34]

Participants

6

Reactant 4

HCID 8022Ethyl isocyanateHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 178434412HCID 178434412, compound

Product 1

HCID 178465274HCID 178465274, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 75 mg 3-Fluoro-4-[3-methyl-4-(3-methyl-[1,4]diazepan-1-ylmethyl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-phenol in 1.5 ml abs. THF were added 15 mg ethyl isocyanate and 26 mg Hünig's base. After 16 h at rt water was added, and the pH was adjusted to neutral. The mixture was extracted with ethyl acetate twice and the combined organic layers were dried and concentrated in vacuo. After purification by HPLC 29 mg (32%) of the title compound were obtained.

Workup

  1. extractionThe mixture was extracted with ethyl acetate twice
  2. customthe combined organic layers were dried
  3. concentrationconcentrated in vacuo
  4. customAfter purification by HPLC 29 mg (32%) of the title compound
  5. customwere obtained

Sources & evidence

ORD record
ord-5ca2aefedac64a8ea4debea34053d9ad
Source dataset
uspto-grants-2015_09
Patent number
US09133181B2

Reaction notes

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