Lysergic Acid → HCID 68542692, compound

HRID 1445719Notes

Reaction equation

HRID 1445719 reaction equation
[CH3:1][C:2]1[NH:19][C:18]2[C:20]3[C:3]=1[CH2:4][C@@H:5]1[C:13]([C:14]=3[CH:15]=[CH:16][CH:17]=2)=[CH:12][C@@H:8]([C:9](=O)[OH:10])[CH2:7][N:6]1[CH3:21].OC([C@@H]1C=C2[C@@H](CC3[C:41]4[C:34](=[CH:35][CH:36]=[CH:37][C:38]2=4)[NH:33]C=3)N(C)C1)=O.[NH:42]1[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1.N1CCCC1.C1(N=C=[O:61])C=CC=CC=1>>[C:34]1([NH:33][C:21]([N:6]2[CH:5]3[C:13]([C:14]4[CH:15]=[CH:16][CH:17]=[C:18]5[C:20]=4[C:3](=[C:2]([CH3:1])[NH:19]5)[CH2:4]3)=[CH:12][CH:8]([C:9]([N:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[O:10])[CH2:7]2)=[O:61])[CH:35]=[CH:36][CH:37]=[CH:38][CH:41]=1

Participants

6

Reactant 5

HCID 6717Lysergic AcidHCID 7672Phenyl isocyanateHCID 8082PiperidineHCID 31268PyrrolidineHCID 13269012HCID 13269012, compound

Product 1

HCID 68542692HCID 68542692, compound

Procedure

5-Methyl-9-(piperidine-1-carbonyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-7-carboxylic acid phenylamide is prepared following similar procedures as described for Example 45 using 2-methyl-lysergic acid (instead of lysergic acid) and piperidine (instead of pyrrolidine) in step 1 and phenyl isocyanate in step 3. MS: 455 (M+H)+

Sources & evidence

ORD record
ord-eac0eb8e4a9141c4897298e2d286440e
Source dataset
uspto-grants-2010_02
Patent number
US07666877B2

Reaction notes

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