1-Hydroxybenzotriazole → HCID 69327386, compound

HRID 1973028Notes

Reaction equation

HRID 1973028 reaction equation
C(N(CC)C(C)C)(C)C.[C:10]([O:14][C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=O)=[O:16])([CH3:13])([CH3:12])[CH3:11].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH2:47]([N:54]1[CH:62]=[C:61]2[C:56]([CH:57]=[C:58]([C:63]3[CH:64]=[C:65]([CH:73]4[CH2:78][CH2:77][NH:76][CH2:75][CH2:74]4)[N:66]4[C:71]=3[C:70]([NH2:72])=[N:69][CH:68]=[N:67]4)[CH:59]=[CH:60]2)=[N:55]1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C>[C:10]([O:14][C:15]([N:17]1[CH2:24][CH2:23][CH2:22][CH:18]1[C:19]([N:76]1[CH2:77][CH2:78][CH:73]([C:65]2[N:66]3[C:71]([C:70]([NH2:72])=[N:69][CH:68]=[N:67]3)=[C:63]([C:58]3[CH:59]=[CH:60][C:61]4[C:56]([CH:57]=3)=[N:55][N:54]([CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH:62]=4)[CH:64]=2)[CH2:74][CH2:75]1)=[O:21])=[O:16])([CH3:11])([CH3:12])[CH3:13]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16066662HCID 16066662, compound

Product 1

HCID 69327386HCID 69327386, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

N,N-Diisopropylethylamine (35.0 μL, 0.200 mmol, 2.0 eq.) was added to N-(tert-butoxycarbonyl)-L-proline (23.7 mg, 0.110 mmol, 1.1 eq), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (19.2 mg, 0.100 mmol, 1.0 eq), 1-hydroxybenzotriazole (13.5 mg, 0.100 mmol, 1.0 eq) and 1 mL of anhydrous DMF. The reaction was cooled to 0° C. and shaken for 30 minutes. Then to this mixture was added 5-(2-benzyl-2H-indazol-6-yl)-7-piperidin-4-ylpyrrolo[2,1-f][1,2,4]triazin-4-amine (42.3 mg, 0.1 mmol, 1.0 eq.) in 1 mL of anhydrous DMF. The reaction was shaken for 5 minutes at 0° C. The reaction was slowly warmed to rt and shaken over night. The product was purified by acidic HPLC on a Sunfire column (5% to 90%, 12 min).

Workup

  1. stirringThe reaction was shaken for 5 minutes at 0° C
  2. temperatureThe reaction was slowly warmed to rt
  3. stirringshaken over night
  4. customThe product was purified by acidic HPLC on a Sunfire column (5% to 90%, 12 min)

Sources & evidence

ORD record
ord-74a636a664324e978d67ed1d9865c86d
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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