Hydrochloric Acid → HCID 66710898, compound

HRID 1261908Notes

Reaction equation

HRID 1261908 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:19]=[CH:18][C:17]4=[CH:20][CH:21]=[C:22]([C:23]5[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=5)[N:16]4[N:15]=3)=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CN(C)C=O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[CH3:54][S:55]([CH2:58][CH2:59][NH2:60])(=[O:57])=[O:56].Cl.Cl.CN(C)CCCN=C=NCC>>[CH3:54][S:55]([CH2:58][CH2:59][NH:60][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][C:23]([C:22]2[N:16]3[C:17]([CH:18]=[N:19][C:14]([NH:13][C:10]4[CH:9]=[CH:8][C:7]([N:1]5[CH2:6][CH2:5][O:4][CH2:3][CH2:2]5)=[CH:12][CH:11]=4)=[N:15]3)=[CH:20][CH:21]=2)=[CH:24][CH:25]=1)(=[O:57])=[O:56]

Participants

8

Reactant 7

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 43405612-(Methylsulfonyl)ethanamineHCID 66710897HCID 66710897, compound

Product 1

HCID 66710898HCID 66710898, compound

Procedure

Into a 30 mL vial, 4-[2-(4-Morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzoic acid (104 mg, 0.251 mmol), N,N-Dimethylformamide (2.08 mL, 26.9 mmol; Supplier=EMD), 1-Hydroxybenzotriazole (41 mg, 0.30 mmol), 4-Methylmorpholine (33.1 uL, 0.301 mmol), [B] 2-Methanesulfonyl-ethylamine; hydrochloride (0.0601 g, 0.376 mmol), and N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.0577 g, 0.301 mmol) were added. The reaction was stirred at room temperature overnight. The reaction was partitioned with sat'd NaHCO3. The precipitate was filtered and washed with water to afford N-(2-Methanesulfonyl-ethyl)-4-[2-(4-morpholin-4-yl-phenylamino)-pyrrolo[2,1-f][1,2,4]triazin-7-yl]-benzamide as a yellow solid. MP 241-242° C. LCMS (E/I+) 521.00M+H). NMR 1H (DSMO-d6)-9.34 (d, 1H, J=2.00), 8.97 (s, 1H), 8.60 (d, 1H, J=8.21 Hz), 8.79 (t, 1H, J=5.72 Hz), 8.34 (d, 2H, J=8.52 Hz), 7.97 (d, 2H, J=8.52 Hz), 7.65 (d, 2H, J=9.00 Hz), 7.28 (d, 1H, J=4.80 Hz), 6.94-7.00 (m, 3H), 3.65-3.80 (m, 6H), 3.41 (t, 2H, J=6.88 Hz), 3.03-3.12 (m, 7H).

Workup

  1. customThe reaction was partitioned with sat'd NaHCO3
  2. filtrationThe precipitate was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-4e74ffe1d0644f22b6181bea2d432478
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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