3-(Dimethylamino)propanoic acid hydrochloride → HCID 58529810, compound

HRID 1972848Notes

Reaction equation

HRID 1972848 reaction equation
[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:31][CH2:30][NH:29][CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:33][N:34]([CH3:40])[CH2:35][CH2:36][C:37](O)=[O:38]>>[CH2:1]([N:8]1[CH:16]=[C:15]2[C:10]([CH:11]=[C:12]([C:17]3[CH:18]=[C:19]([CH:27]4[CH2:31][CH2:30][N:29]([C:37](=[O:38])[CH2:36][CH2:35][N:34]([CH3:40])[CH3:33])[CH2:28]4)[N:20]4[C:25]=3[C:24]([NH2:26])=[N:23][CH:22]=[N:21]4)[CH:13]=[CH:14]2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 115863273-(Dimethylamino)propanoic acid hydrochlorideHCID 58529326HCID 58529326, compound

Product 1

HCID 58529810HCID 58529810, compoundYield 18.3%

Procedure

5-(2-benzyl-2H-indazol-6-yl)-7-pyrrolidin-3-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (75 mg, 0.183 mmol) was coupled to N,N-dimethyl-beta-alanine hydrochloride (29 mg, 0.189 mmol) following the procedure described in step 1 of Example 120. The product was purified via HPLC using a Sunfire Prep C18 OBD 5 micron, 30×75 mm column. The compound was eluted using a gradient 10-70% acetonitrile/water with 0.1% TFA over 20 minutes to yield (17 mg, 18%) title compound. 1H NMR (300 MHz, DMSO-d6) δ 8.53 (s, 1 H), 7.92 (s, 1 H), 7.79 (d, 1 H), 7.58 (s, 1 H), 7.36-7.32 (m, 4 H), 7.14 (d, 1 H), 6.68 (d, 1 H), 5.64 (s, 2 H), 4.00-3.30 (m, 9 H), 2.45-2.05 (m, 2H), 2.07 (s, 6 H); ES-MS m/z 509.2 [M+H]+, HPLC RT (min) 2.11.

Workup

  1. customThe product was purified via HPLC
  2. washThe compound was eluted
  3. customover 20 minutes

Sources & evidence

ORD record
ord-7669671b2a5c403aa9a55ab8024287c5
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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