1,3-Propanediamine → HCID 10164511, compound

HRID 1373838Notes

Reaction equation

HRID 1373838 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:23]([C:24]3[CH:29]=[CH:28][N:27]=[C:26](F)[CH:25]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18](F)[CH:17]=4)[N:10]3[N:9]=2)=[CH:4][CH:3]=1.[NH2:31][CH2:32][CH2:33][CH2:34][NH2:35]>>[NH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:26]1[CH:25]=[C:24]([C:23]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:9][N:10]3[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:9][CH2:8][CH2:23][CH2:11][NH2:10])[CH:17]=4)=[CH:14][CH:13]=[CH:12][C:11]=23)[CH:29]=[CH:28][N:27]=1

Participants

3

Reactant 2

HCID 4281,3-PropanediamineHCID 10157930HCID 10157930, compound

Product 1

HCID 10164511HCID 10164511, compoundYield 46%

Procedure

A solution of 2-(4-fluorophenyl)-3,7-bis(2-fluoropyridin-4-yl)pyrazolo[1,5-α]pyridine (34 mg, 0.08 mmol) in 1,3-diaminopropane (1 mL) was heated at 150° C. for 0.25 hours. Upon cooling to room temperature, the mixture was concentrated in vacuo and the residue was triturated with hot ethyl acetate. The resulting solids were collected on filter, washed with ethyl ether and dried to provide N-{4-[3-{2-[(3-aminopropyl)amino]pyridin-4-yl}-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-7-yl]pyridin-2-yl}propane-1,3-diamine as a light yellow powder (19 mg, 46%). 1H NMR (CD3OD): δ 8.18 (d, 1H), 8.03 (d, 1H), 7.78 (d, 1H), 7.65 (dd, 2H), 7.45 (dd, 1H), 7.30 (s, 1H), 7.1–7.2 (m, 4H), 6.60 (s, 1H), 6.59 (d, 1H), 3.55 (t, 2H), 3.47 (t, 2H), 3.0 (q, 4H), 1.88–2.04 (m, 4H); MS m/z 511 (M+1).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residue was triturated with hot ethyl acetate
  3. customThe resulting solids were collected
  4. filtrationon filter
  5. washwashed with ethyl ether
  6. customdried

Sources & evidence

ORD record
ord-20ecc05d187d4db890cf0dcba5183a6c
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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