2-(6-Amino-3,4-dihydroisoquinolin-2(1H)-yl)acetamide → 2-{6-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-3,4-dihydro-1H-isoquinolin-2-yl}-acetamide

HRID 1262147Notes

Reaction equation

HRID 1262147 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15](O)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[NH2:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[CH2:26][N:25]([CH2:30][C:31]([NH2:33])=[O:32])[CH2:24][CH2:23]2>>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15]([NH:19][C:20]4[CH:21]=[C:22]5[C:27](=[CH:28][CH:29]=4)[CH2:26][N:25]([CH2:30][C:31]([NH2:33])=[O:32])[CH2:24][CH2:23]5)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 574160652-(6-Amino-3,4-dihydroisoquinolin-2(1H)-yl)acetamideHCID 178488500HCID 178488500, compound

Product 1

HCID 667122542-{6-[7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-3,4-dihydro-1H-isoquinolin-2-yl}-acetamide

Procedure

7-(6-Methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (0.0609 g, 0.251 mmol) and 2-(6-Amino-3,4-dihydro-1H-isoquinolin-2-yl)-acetamide (0.064 g, 0.31) were reacted in an analogous manner to Example 908D at 50° C. for 16 h. The reaction mixture was concentrated and purified by Gilson RP-HPLC. HPLC rt=2.083 min, purity=91%. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 10.23 (bs, 1H), 9.63 (s, 1H), 9.10 (s, 1H), 9.01 (s, 1H), 8.44 (dd, J=8.9 Hz, 2.2 Hz, 1H), 7.96 (s, 1H), 7.91 (s, 1H), 7.75 (s, 1H), 7.40 (d, J=8.9 Hz, 1H), 7.21 (d, J=4.4 Hz, 1H), 7.13 (d, J=8.9 Hz, 1H), 7.04 (d, J=8.6 Hz, 1H), 6.98 (d, J=4.5 Hz, 1H), 4.50 (m, 1H), 4.33 (m, 1H), 4.05 (m, 2H), 3.95 (s, 3H), 3.70 (m, 1H), 3.43 (m, 1H), 3.23 (m, 1H), 3.08 (m, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by Gilson RP-HPLC
  3. customHPLC rt=2.083 min, purity=91%

Sources & evidence

ORD record
ord-537bf16cdfe04623a2b195da9503698c
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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