2-Chloro-6-methylquinoline-3-carboxaldehyde → HCID 11294461, compound

HRID 1181301Notes

Reaction equation

HRID 1181301 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:21]=[C:9]2[N:10]=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[N:12]=[C:13]([NH2:14])[N:8]2[N:7]=1.[Cl:22][C:23]1[C:32]([CH:33]=O)=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([CH3:35])[CH:29]=2)[N:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[Cl:22][C:23]1[C:32]([CH2:33][N:18]2[CH2:17][CH2:16][N:15]([C:11]3[N:12]=[C:13]([NH2:14])[N:8]4[N:7]=[C:6]([C:2]5[O:1][CH:5]=[CH:4][CH:3]=5)[CH:21]=[C:9]4[N:10]=3)[CH2:20][CH2:19]2)=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([CH3:35])[CH:29]=2)[N:24]=1

Participants

6

Reactant 3

HCID 6890812-Chloro-6-methylquinoline-3-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 694325217-Furan-2-yl-2-piperazin-1-yl-pyrazolo[1,5-a][1,3,5]triazin-4-ylamine

Product 1

HCID 11294461HCID 11294461, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

7-Furan-2-yl-2-piperazin-1-yl-pyrazolo[1,5-a][1,3,5]triazin-4-ylamine (0.15 mmol) was dissolved in 4 mL of CH2Cl2 along with 2 eq. of 2-chloro-6-methyl-quinoline-3-carbaldehyde and 25 mL of glacial acetic acid. The reaction mixture was stirred at room temperature for 30 minutes and sodium triacetoxyborohydride (4 eq.) was added in a single portion. The resulting reaction mixture was then stirred at room temperature for 18 hours. It was then concentrated under a stream of N2 and purified by preparative HPLC using a mixture of aqueous CH3CN that has been buffered with 0.1% TFA. 1H NMR (DMSO-d6) δ 7.60 (d, J=1.0 Hz, 1H), 7.28 (br s, 2H), 7.22 (d, J=3.6 Hz, 1H), 7.4-8.0 (m, 4H), 6.68 (dd, J=3.6 Hz, 1.0 Hz, 1H), 6.2 (s, 1H) 3.8 (br s, 2H), 2.2-3.2 (m, 8H), 2.35 (br s, 3 H). MS: m/z: 476 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas then stirred at room temperature for 18 hours
  3. concentrationIt was then concentrated under a stream of N2
  4. custompurified by preparative HPLC
  5. additiona mixture of aqueous CH3CN that

Sources & evidence

ORD record
ord-7e9a3df6dc53471e8ab474070f4336d3
Source dataset
uspto-grants-2007_10
Patent number
US07285550B2

Reaction notes

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