Ethyl formate → HCID 22390518, compound

HRID 1072085Notes

Reaction equation

HRID 1072085 reaction equation
C1(S([CH2:9][C:10]2[CH:11]=[CH:12][N:13]3[C:18]=2[C:17]([NH:19][C:20]2[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=2)[N:25]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)[N:24]=[CH:23]4)=[N:16][CH:15]=[N:14]3)=O)C=CC=CC=1.[NH2:37][CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.[CH:44](OCC)=[O:45]>>[F:36][C:32]1[CH:31]=[C:30]([CH:35]=[CH:34][CH:33]=1)[CH2:29][N:25]1[C:26]2[C:22](=[CH:21][C:20]([NH:19][C:17]3[C:18]4=[C:10]([CH2:9][N:41]5[CH2:42][CH2:43][CH:38]([NH:37][CH:44]=[O:45])[CH2:39][CH2:40]5)[CH:11]=[CH:12][N:13]4[N:14]=[CH:15][N:16]=3)=[CH:28][CH:27]=2)[CH:23]=[N:24]1

Participants

4

Reactant 3

HCID 8025Ethyl formateHCID 4243614-PiperidinamineHCID 22390503HCID 22390503, compound

Product 1

HCID 22390518HCID 22390518, compoundYield 36%

Procedure

A mixture of (5-benzenesulfinylmethyl-pyrrolo[2,1-f][1,2,4]triazin-4-yl)-[1-(3-fluoro-benzyl)-1H-indazol-5-yl]-amine (200 mg, 0.4 mmole) and 4-amino-piperidine (1.2 g, 30 equiv.) in a vial was placed in microwave reactor (Personal Chemistry's Smith Creator) and irradiated at 150° C. for 20 min. Ethyl formate (3 ml) was added to above mixture and irradiation was continued at 135° C. for 30 min. Concentration of the reaction mixture followed by preparative HPLC purification afforded N-(1-{4-[1-(3-fluoro-benzyl)-1H-indazol-5-ylamino]-pyrrolo[2,1-f][1,2,4]triazin-5-ylmethyl}-piperidin-4-yl)-formamide (71 mg, 36%). This was dissolved in dry THF (0.3 ml) and added dropwise to a stirred solution of LiAlH4 (1M in ether, 0.57 ml, 4 equiv.). Water (0.5 mL) was slowly added after 20 hr and the title compound (16 mg, 23%) was isolated by preparative HPLC. MS: 485 (M+H)+; HPLC Ret Time: 1.02 min (Xterra 3.0×50 mm S7 C18 column, 2 min gradient, 5 ml/min).

Workup

  1. customwas placed in microwave reactor
  2. custom(Personal Chemistry's Smith Creator) and irradiated at 150° C. for 20 min
  3. customConcentration of the reaction mixture followed by preparative HPLC purification

Sources & evidence

ORD record
ord-a5284faa2b1e4a28831ea0fbbe44a77c
Source dataset
uspto-grants-2005_06
Patent number
US06908916B2

Reaction notes

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